p-Fluorophenethylamine → (s)-{[(4-Fluorobenzyl)methylcarbamoyl]phenylmethyl}carbamic acid tert-butyl ester

HRID 2221467노트

반응식

HRID 2221467 반응식
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:16]([OH:18])=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])[CH3:3].[F:19][C:20]1[CH:28]=[CH:27][C:23]([CH2:24][CH2:25][NH2:26])=[CH:22][CH:21]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:2]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:16](=[O:18])[NH:26][CH2:25][CH2:24][C:23]1[CH:27]=[CH:28][C:20]([F:19])=[CH:21][CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([CH3:1])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 4653p-FluorophenethylamineHCID 2733179PyBroPHCID 2755953(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid

생성물 1

HCID 69267743(s)-{[(4-Fluorobenzyl)methylcarbamoyl]phenylmethyl}carbamic acid tert-butyl ester수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N-Boc-L-phenylglycine (H, 17.2 g, 68.5 mmol) and (4-fluorobenzyl)methylamine (10.47 g, 75.3 mmol) in CH2Cl2 (550 mL) was cooled to 0° C. Disopropylethylamine (35.8 mL, 205 mmol) and PyBroP (38.3 g, 82.1 mmol) were then added sequentially. The cooling bath was removed and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the title compound (24.5 g, 96%) was isolated by chromatography on silica gel eluting with a gradient of 40% to 60% ethyl acetate in hexane. 1H NMR (selected signals, CDCl3): □6.02 (d, 0.3H), 5.56 (d, 0.7H), 2.83 (s, 0.9H), 2.78 (s, 2.1H), 1.40 (s, 6.3 H, 1.39 (s, 2.7H).

후처리

  1. customThe cooling bath was removed
  2. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-d7c7c852f91c4e6c8b43812366c65384
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368573B2

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