| Identification | Back Directory | [Name]
PEG4-tert-butyl acetate | [CAS]
169751-72-8 | [Synonyms]
OH-PEG4-CH2COOH
OH-PEG4-CH2COOtBu
HO-PEG4-CH2COOtBu
HO-PEG4-CH2CO2t-Bu
PEG5-t-butyl acetate
Hydroxy-PEG4-CH2-Boc
Hydroxy-PEG4-CH2CO2tBu
Hydroxy-PEG4-CH2COOtBu
PEG4-tert-butyl acetate
PEG5-tert-butyl acetate
Hydroxy-PEG4-t-butyl acetate
tert-butyl 14-hydroxy-3,6,9,12-tetraoxatetradecanoate
tert-butyl 14-hydroxy-3,6,9,12-tetraoxatetradecan-1-oate
3,6,9,12-Tetraoxatetradecanoic acid, 14-hydroxy-, 1,1-dimethylethyl ester | [Molecular Formula]
C14H28O7 | [MDL Number]
MFCD27635170 | [MOL File]
169751-72-8.mol | [Molecular Weight]
308.37 |
| Chemical Properties | Back Directory | [Boiling point ]
393.1±32.0 °C(Predicted) | [density ]
1.077±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Soluble in Water, DMSO, DCM, DMF | [form ]
Liquid | [pka]
14.36±0.10(Predicted) | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Description]
Hydroxy-PEG4-CH2CO2tBu is a PEG linker containing a hydroxyl group with a t-butyl protected carboxyl group. The hydrophilic PEG spacer increases solubility in aqueous media. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. The t-butyl protected carboxyl group can be deprotected under acidic conditions. | [Uses]
Hydroxy-PEG4-CH2-Boc is a PEG-based PROTAC linker can be used in the synthesis of PROTACs. | [Synthesis]
GENERAL STEPS: To a stirred mixture of tert-butyl 2-bromoacetate (5.4 mL, 36.6 mmol) and 2,2'-((oxo-bis(ethane-2,1-diyl))bis(oxy))diethanol (35.0 mL, 203 mmol) in DMSO (50 mL) was added in two additions of NaH (1.6217 g, 40.6 mmol, a 60% oil solution). The reaction mixture was slowly warmed to room temperature with continuous stirring for 23 hours. Subsequently, the reaction solution was diluted with water (50 mL), saturated with NaCl (50 g), stirred for 5 min and extracted with ether (3 x 100 mL). The organic phases were combined and concentrated. The residue was dissolved in dichloromethane (50 mL) and water (25 mL) and stirred for 5 minutes. The organic phases were separated by a phase separator, concentrated, and purified using an 80 g silica gel column with a gradient of ethyl acetate in hexanes as eluent (50-100%) to afford tert-butyl 14-hydroxy-3,6,9,12-tetraoxatetradecane-1-carboxylate (8.2 g, 72.7% yield) as a light yellow oil. rf = 0.08 (ethyl acetate). NMR hydrogen spectrum (400 MHz, CDCl3) δ 4.02 (d, J = 1.0 Hz, 2H), 3.75-3.60 (m, 12H), 1.47 (s, 9H) ppm. low-resolution mass spectrometry (ESI) m/z: C14H28O7 Calculated value: 308.3679; Measured value: 330.95 (M + Na)+; Measured value: 347.01 (M + K)+. | [References]
[1] Patent: WO2018/200981, 2018, A1. Location in patent: Paragraph 0209; 0294-0295
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 2, p. 583 - 598
[3] Patent: US2018/177750, 2018, A1. Location in patent: Paragraph 1106 |
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