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 1814035ノート

反応式

HRID 1814035 の反応式
[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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e08a53b80d5c4aae8b12e116d32cbe4c
出典データセット
uspto-grants-2005_04
特許番号
US06875784B2

反応ノート

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