Diethyl Ether → tert-butyl (1S,3S)-3-{[difluoro(4-methylphenyl)acetyl]amino}cyclopentylcarbamate

HRID 271391ノート

反応式

HRID 271391 の反応式
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3]1.[F:15][C:16]([F:29])([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[C:17](OCC)=[O:18].CCOCC.CCCCCC>CCO>[F:15][C:16]([F:29])([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[C:17]([NH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:3]1)=[O:18]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 14888699Ethyl 2,2-difluoro-2-(p-tolyl)acetateHCID 45091937tert-Butyl N-((1S,3S)-3-aminocyclopentyl)carbamate

生成物 1

HCID 59834916tert-butyl (1S,3S)-3-{[difluoro(4-methylphenyl)acetyl]amino}cyclopentylcarbamate収率 42%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of tert-butyl [(1S,3S)-3-aminocyclopentyl]carbamate (1.36 g, 6.8 mmol) and ethyl difluoro(4-methylphenyl)acetate (1.45 g, 6.8 mmol) in EtOH (5 mL) was stirred at reflux for 16 h. The solution was cooled to rt. whereupon it solidified. Et2O (6 mL) and hexane (3 mL) were added and the mixture was stirred for 3 h and the solids collected by filtration, rinsing with Et2O (2 mL), and dried to give the title compound (1.051 g) as a solid; MS=313.4 (M+1-isobutylene).

後処理

  1. temperatureat reflux for 16 h
  2. filtrationthe solids collected by filtration
  3. washrinsing with Et2O (2 mL)
  4. customdried

出典と根拠

ORDレコード
ord-e8e34dd190884ddc986aaa8d68156ca6
出典データセット
uspto-grants-2008_11
特許番号
US07452893B2

反応ノート

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