| Identification | Back Directory | [Name]
5-Bromo-N-[(tert-butoxy)carbonyl]-L-norvaline tert-butyl ester | [CAS]
91229-86-6 | [Synonyms]
N-Boc-5-bromo-L-norvaline tert-butyl ester
5-Bromo-N-[(tert-butoxy)carbonyl]-L-norvaline tert-butyl ester
(S)-tert-Butyl 5-broMo-2-((tert-butoxycarbonyl)aMino)pentanoate
5-Bromo-N-[(tert-butoxy)carbonyl]-L-norvaline tert-butyl ester USP/EP/BP
ert-butyl(2S)-5-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
L-Norvaline, 5-bromo-N-[(1,1-dimethylethoxy)carbonyl]-, 1,1-dimethylethyl ester | [Molecular Formula]
C14H26BrNO4 | [MDL Number]
MFCD22576481 | [MOL File]
91229-86-6.mol | [Molecular Weight]
352.26 |
| Chemical Properties | Back Directory | [Boiling point ]
402.7±40.0 °C(Predicted) | [density ]
1.218 | [storage temp. ]
2-8°C | [pka]
11.05±0.46(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of tert-butyl (S)-5-bromo-2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate from (S)-2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoic acid is as follows:
1. tert-Butyl (S)-2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate (210.2 mg) was dissolved in dichloromethane (7.3 mL) and cooled to 0°C.
2. Carbon tetrabromide (1.5 eq.) and triphenylphosphine (2.0 eq.) were added sequentially and the reaction mixture was stirred at 0 °C for 20 min.
3. Upon completion of the reaction, the reaction was terminated with hexane/ethyl acetate (2:1, v/v).
4. The reaction mixture was purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 2:1, v/v) to afford 254.6 mg (S)-tert-butyl 5-bromo-2-((tert-butoxycarbonyl)amino)pentanoate in 100% yield as a colorless oil. | [References]
[1] Patent: EP2952504, 2015, A1. Location in patent: Paragraph 0151-0152
[2] European Journal of Organic Chemistry, 2004, # 21, p. 4391 - 4396
[3] Journal of Organic Chemistry, 1984, vol. 49, # 19, p. 3527 - 3534
[4] Chemistry Letters, 1996, # 8, p. 621 - 622 |
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