Acetic Acid → HCID 58458628, 화합물

HRID 44220노트

반응식

HRID 44220 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 58458628HCID 58458628, 화합물수율 93%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b29c9c3561044cee80cc26c5c4262cae
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541407B2

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