Methanol → {(5S)-3-[3,5-difluoro-4-(6-oxa-3-azabicyclo[3.1.0]hex-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl acetamide

HRID 1814035노트

반응식

HRID 1814035 반응식
[O-][CH2:2][CH2:3]CC.[Li+].C([O:14][C:15](=[O:31])[NH:16][C:17]1[CH:22]=[C:21]([F:23])[C:20]([N:24]2[CH2:29][CH:28]3[CH:26]([O:27]3)[CH2:25]2)=[C:19]([F:30])[CH:18]=1)C1C=CC=CC=1.C[OH:33].C([NH:37][CH2:38][C@H:39](OC(=O)C)[CH2:40]Cl)(=O)C>CN(C=O)C.C1COCC1>[F:30][C:19]1[CH:18]=[C:17]([N:16]2[CH2:3][C@H:2]([CH2:40][CH2:39][C:38]([NH2:37])=[O:33])[O:14][C:15]2=[O:31])[CH:22]=[C:21]([F:23])[C:20]=1[N:24]1[CH2:25][CH:26]2[CH:28]([O:27]2)[CH2:29]1

참가 물질

7

반응물 4

HCID 887MethanolHCID 7357675(2S)-1-Acetamido-3-chloropropan-2-yl acetateHCID 20770994[3,5-Difluoro-4-(6-oxa-3-aza-bicyclo[3.1.0]hex-3-yl)-phenyl]-carbamic acid benzyl esterHCID 23676864Lithium butan-1-olate

생성물 1

HCID 86593189{(5S)-3-[3,5-difluoro-4-(6-oxa-3-azabicyclo[3.1.0]hex-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl acetamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

Lithium butoxide solution (1.9 mL of a 1.0 M THF solution, 1.9 mmol) was added to a cooled (0° C.) solution of [3,5-difluoro-4-(6-oxa-3-aza-bicyclo[3.1.0]hex-3-yl)-phenyl]-carbamic acid benzyl ester (0.22 g, 0.64 mmol) in DMF (0.43 mL) and MeOH (0.05 mL, 1.2 mmol). Solid (S)-acetic acid 2-acetylamino-1-chloromethyl-ethyl ester (0.25 g, 1.27 mmol) was then added and the solution allowed to warm to room temperature and stirred for 16 h. The reaction mixture was quenched with sat. NH4Cl and extracted with ethyl acetate. The organic layers were washed with water, brine and dried (MgSO4). The title compound was isolated by silica gel chromatography (0-3% MeOH/dichloromethane).

후처리

  1. customThe reaction mixture was quenched with sat. NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried (MgSO4)

출처 및 근거

ORD 기록
ord-e08a53b80d5c4aae8b12e116d32cbe4c
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875784B2

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