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

HRID 2221467ノート

反応式

HRID 2221467 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-d7c7c852f91c4e6c8b43812366c65384
出典データセット
uspto-grants-2008_05
特許番号
US07368573B2

反応ノート

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