Acetic Acid → HCID 58458628、化合物

HRID 44220ノート

反応式

HRID 44220 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:24][Si](C)(C)C)=[N-].C(O)(=O)C>ClCCl.CO>[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:24])=[O:18])=[CH:20][CH:21]=2)[CH2:10][CH2:11][CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 583451244-{1-[(tert-Butoxycarbonyl)amino]cyclobutyl}benzoic acid

生成物 1

HCID 58458628HCID 58458628、化合物収率 93%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)benzoic acid (15 g, 52 mmol) in dichloromethane (200 mL) and methanol (50 mL), cooled at 0° C., was added in a dropwise manner a 2 M solution of diazomethyl trimethylsilane in hexanes (28 mL, 57 mmol). The reaction mixture was stirred at room temperature for one hour before the addition, at 0° C., of acetic acid (10 mL). The mixture was washed with saturated aqueous sodium bicarbonate solution until the aqueous phase remained basic. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo, yielding the methyl 4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)benzoate as a white crystalline solid (14.8 g, 93%). M.p.=90° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.91 (d, J=7.6 Hz, 2H), 7.74 (s, 1H), 7.50 (d, J=8.0 Hz, 2H), 3.84 (s, 3H), 2.38 (br.s, 4H), 2.1-1.9 (m, 1H), 1.85-1.7 (m, 1H), 1.32 (br.s, 9H); LCMS [M-tBu+H]: 250.

後処理

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate solution until the aqueous phase
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b29c9c3561044cee80cc26c5c4262cae
出典データセット
uspto-grants-2013_09
特許番号
US08541407B2

反応ノート

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