Acetic Acid → HCID 57611030, 화합물

HRID 709358노트

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HRID 709358 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][NH:10][C:11]([C@@H:13]2[CH2:17][C:16]([F:19])([F:18])[CH2:15][N:14]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=O)=[CH:4][CH:3]=1.C(O)(=O)C.C(O)(=O)C.[NH3:36].C1(C)C(C)=CC=CC=1>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:36][C:11]([C@@H:13]3[CH2:17][C:16]([F:19])([F:18])[CH2:15][N:14]3[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:10][CH:9]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7237O-XyleneHCID 12432Ammonia acetateHCID 59166348(S)-tert-butyl 2-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-4,4-difluoropyrrolidine-1-carboxylate

생성물 1

HCID 57611030HCID 57611030, 화합물수율 102.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
140 °C

실험 절차

In a 50 mL seal tube, (S)-tert-butyl 2-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-4,4-difluoropyrrolidine-1-carboxylate (1.8 g, 4.02 mmol) and acetic acid, ammonia acetate salt (1.55 g, 20.1 mmol) were combined with xylene (16 ml). The reaction mixture was heated to 140° C. and stirred for 4 hr. The reaction mixture was cooled and diluted with EtOAc (50 ml). It was washed with water and brine, dried with MgSO4, concentrated and purified on a silica gel column (CH2Cl2, 30%, 50%, 80% EtOAc/CH2Cl2) to afford (S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4,4-difluoropyrrolidine-1-carboxylate as a yellow solid (1.77 g, 74%): ESI-LRMS m/e calcd for C18H22BrF2N3O2 [M+] 428. found 429 [M+H+].

후처리

  1. customIn a 50 mL seal tube
  2. temperatureThe reaction mixture was cooled
  3. washIt was washed with water and brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. custompurified on a silica gel column (CH2Cl2, 30%, 50%, 80% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-8bf8f2abd84541d795828cc9dc807833
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09180193B2

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