| Identification | More | [Name]
Boc-L-aspartic acid 4-tert-butyl ester | [CAS]
1676-90-0 | [Synonyms]
BOC-ASPARTIC ACID(OTBU)-OH
BOC-ASP(OBUT)-OH
BOC-ASP-OTBU
BOC-ASP(OTBU)-OH
BOC-L-ASPARTIC ACID 4-TERT-BUTYL ESTER
BOC-L-ASPARTIC ACID-BETA-T-BUTYL ESTER
BOC-L-ASP(OTBU)-OH
BOC-L-ASP(TBU)-OH
N-ALPHA-T-BOC-L-ASPARTIC ACID BETA-T-BUTYL ESTER
N-ALPHA-T-BUTOXYCARBONYL-L-ASPARTIC ACID-4-T-BUTYL ESTER
N-ALPHA-T-BUTOXYCARBONYL-L-ASPARTIC ACID-BETA-T-BUTYL ESTER
N-ALPHA-T-BUTYLOXYCARBONYL-L-ASPARTIC ACID BETA-T-BUTYL ESTER
N-ALPHA-TERT-BUTYLOXYCARBONYL-L-ASPARTIC ACID BETA-TERT-BUTYL ESTER | [Molecular Formula]
C13H23NO6 | [MDL Number]
MFCD00076912 | [Molecular Weight]
289.32 | [MOL File]
1676-90-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
64-67 °C
| [alpha ]
2 º (c=1% in MeOH) | [Boiling point ]
432.6±40.0 °C(Predicted) | [density ]
1.139±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Soluble in methanol and dimethyl sulfoxide. | [form ]
Powder | [pka]
3.69±0.23(Predicted) | [color ]
White | [Optical Rotation]
[α]20/D +2.0±0.4°, c = 1% in methanol | [BRN ]
2336144 | [InChI]
InChI=1S/C13H23NO6/c1-12(2,3)19-9(15)7-8(10(16)17)14-11(18)20-13(4,5)6/h8H,7H2,1-6H3,(H,14,18)(H,16,17)/t8-/m0/s1 | [InChIKey]
PHJDCONJXLIIPW-QMMMGPOBSA-N | [SMILES]
C(O)(=O)[C@H](CC(OC(C)(C)C)=O)NC(OC(C)(C)C)=O | [CAS DataBase Reference]
1676-90-0(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
It is used in the preparation of highly selective thrombin inhibitors. Also used in the preparation of thiopeptides and thioacylating agents. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
2.1. Preparation of Boc-Asp(O-tBu)-NCA (II-a)
The method involves the main chain cyclization of a free carboxylic acid in which the amine functional group is protected by Boc. First, (Boc)2-Asp(Ot-Bu)-OH (VII-a) needs to be prepared. The specific steps are as follows:
1. esterify the α-carboxylic acid of Boc-Asp(Ot-Bu)-OH (Va) to benzyl ester (VI-a).
2. reaction with Boc2O in the presence of DMAP to give the bis-Boc-protected amino compound (VII-a).
3. removal of the benzyl ester protecting group by hydrogenation to give (VIII-a).
Subsequent steps include cyclization with Vilsmeier salt protected amino acid (VIII-a). The optimum reaction conditions were in acetonitrile with the salt formed from DMF and oxalyl chloride. The final compound (II-a) was obtained in 90% yield. | [References]
[1] Patent: US2010/16631, 2010, A1. Location in patent: Page/Page column 5-6
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4975 - 4978
[3] Patent: WO2017/24009, 2017, A1. Location in patent: Paragraph 0652
[4] Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 5, p. 283 - 287
[5] Bioorganicheskaya Khimiya, 1999, vol. 25, # 5, p. 323 - 328 |
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