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 1814035Notes

Reaction equation

HRID 1814035 reaction equation
[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

Participants

7

Reactant 4

HCID 887MethanolHCID 7357675(2S)-1-Acetamido-3-chloropropan-2-yl acetateHCID 20770994HCID 20770994, compoundHCID 23676864Lithium butan-1-olate

Product 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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e08a53b80d5c4aae8b12e116d32cbe4c
Source dataset
uspto-grants-2005_04
Patent number
US06875784B2

Reaction notes

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