| Identification | Back Directory | [Name]
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid | [CAS]
135042-12-5 | [Synonyms]
BOC-D-CISHYP-OH
Boc-cis-D-Hyp-OH
cis-Boc-D-Hyp-OH
N-Boc-D-cis-Hyp-OH
N-Boc-cis-D-Hyp-OH
ATTERCOP-CHM AT700573
Boc-cis-4-hydroxy-D-proL
BOC-CIS-4-HYDROXY-D-PROLINE
N-BOC-CIS-4-HYDROXY-D-PROLINE
N-BOC-CIS-6-HYDROXY-D-PROLINE
cis-N-Boc-4-hydroxy-D-proline
N-T-BOC-CIS-4-HYDROXY-D-PROLINE
(2R,4R)-N-BOC-4-HYDROXY-D-PROLINE
N-Boc-cis-4-hydroxy-D-proline 95+%
(Tert-Butoxy)Carbonyl cis-D-Hyp-OH
(2R,4R)-N-Boc-cis-4-hydroxy-D-proline
(2R,4R)N-Boc-trans-4-hydroxy-D-proline
N-α-(t-Butoxycarbonyl)-cis-4-hydroxy-D-proline
N-ALPHA-BUTOXYCARBONYL-CIS-4-HYDROXY-D-PROLINE
cis-N-(tert-Butoxycarbonyl)-4-hydroxy-D-proline
(4R)-1-(tert-Butoxycarbonyl)-4-hydroxy-D-proline
(2r,4r)-n-boc-4-hydroxypyrrolidine-2-carboxylic acid
(2R,4R)-N-Boc-4-hydroxy-2-pyrrolidinecarboxylic acid
BOC-(2R,4R)-(+)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid USP/EP/BP
(2R,4R)-1-tert-Butoxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid
(2R,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
(2R,4R)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-diMethylethyl) ester, (2R,4R)-
1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-diMethylethyl) ester, (2R-cis)- | [EINECS(EC#)]
621-971-2 | [Molecular Formula]
C10H17NO5 | [MDL Number]
MFCD02094407 | [MOL File]
135042-12-5.mol | [Molecular Weight]
231.25 |
| Chemical Properties | Back Directory | [Melting point ]
145°C | [alpha ]
+48～+52°(c=0.67,MeOH,24℃) | [Boiling point ]
390.9±42.0 °C(Predicted) | [density ]
1.312 | [storage temp. ]
2-8°C | [form ]
powder to crystal | [pka]
3.80±0.40(Predicted) | [color ]
White to Light yellow | [Optical Rotation]
[α]22/D +50.0°, c = 1 in methanol | [InChIKey]
BENKAPCDIOILGV-RNFRBKRXSA-N |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
N-Boc-cis-4-hydroxy-D-proline can be used:
- As a starting material in the synthesis of DNA mimicking pyrrolidine peptide nucleic acid (PNA) analog.
- In the synthesis of biologically important macrocyclic dilactones.
- As an intermediate in the synthesis of histamine H3?receptor antagonists.
| [Synthesis]
(2R,4R)-4-Hydroxypyrrolidine-2-carboxylic acid hydrochloride (0.50 g, 3.0 mmol) was dissolved in 6 mL of THF/H2O (2:1) mixed solvent, followed by the addition of 10% NaOH aqueous solution (1.25 mL) for neutralization. Next, di-tert-butyl dicarbonate (0.95 g, 4.42 mmol) was added to the reaction system. The reaction mixture was stirred at room temperature overnight and then the THF was removed by rotary evaporator.The residue was adjusted to pH 2 with 10% aqueous KHSO4 solution and then extracted with ethyl acetate several times. The organic phases were combined, washed sequentially with water and saturated saline and dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure to give (2R,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (542 mg, 78%) as a slurry, which was used directly in the next step of the reaction. [α]D25 = +15.3 (c 1.02, MeOH). IR (thin film method): νmax 3462, 2976, 2934, 1740, 1639 cm?1. 1H NMR (400 MHz, CDCl3) δ 7.22 (br s, 1H), 5.11-5.09 (m, 2H), 4.94-4.93 (m, 1H) , 4.40 (s, 1H), 3.64-3.62 (m, 1H), 3.49-3.44 (m, 2H), 2.27-1.90 (s, 9H).13C NMR (100 MHz, CDCl3) δ 172.47, 151.74, 75.81, 67.15, 55.24, 52.27, 35.97, 25.63 ppm. HRMS (ESI): m/z [M + H]+ calcd for C10H18NO5 232.1185; found 232.1171. | [IC 50]
Non-cleavable Linker | [References]
[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 681 - 694
[2] Journal of the American Chemical Society, 2013, vol. 135, # 11, p. 4333 - 4363
[3] Tetrahedron Asymmetry, 2015, vol. 26, # 20, p. 1156 - 1166
[4] Patent: TW2017/8221, 2017, A. Location in patent: Page/Page column 92; 93 |
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