Benzyl chloroformate → HCID 20681205, 화합물

To a stirred solution of α-methyl-D,L-glutamic acid (10 g, 62 mmol) in 2 N sodium hydroxide (62 mL) at 0–5° C. was added benzyl chloroformate (12.7 g, 74.4 mmol) over 30 min. After the addition was complete the reaction mixture was stirred at room temperature for 3 hours. During this time the pH was maintained at 11 by addition of 2 N sodium hydroxide (33 mL). The reaction mixture was then extracted with ether (60 mL). The aqueous layer was cooled in an ice bath and then acidified with 4N hydrochloric acid (34 mL) to pH=1. The resulting mixture was extracted with ethyl acetate (3×100 mL). The combined ethyl acetate extracts were washed with brine (60 mL) and dried (MgSO4). The solvent was removed in vacuo to give 15.2 g (83%) of N-benzyloxycarbonyl-α-methylglutamic acid as an oil: 1H NMR (CDCl3) δ 8.73(m, 5H), 5.77(b, 1H), 5.09(s, 2H), 2.45–2.27(m, 4H), 2.0(s, 3H).

1. additionAfter the addition
2. extractionThe reaction mixture was then extracted with ether (60 mL)
3. temperatureThe aqueous layer was cooled in an ice bath
4. extractionThe resulting mixture was extracted with ethyl acetate (3×100 mL)
5. washThe combined ethyl acetate extracts were washed with brine (60 mL)
6. dry with materialdried (MgSO4)
7. customThe solvent was removed in vacuo

ORD 기록

ord-618e90e4302a42f5a75fc0e505246df7

출처 데이터셋

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07041680B2