Acetic Acid → 4-tert-butyl 6-methyl (6R,7R)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4,6-dicarboxylate

HRID 1022679Notes

Reaction equation

HRID 1022679 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C@@H:13]([C:15]([OH:17])=[O:16])[C@H:12]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>C1(C)C=CC=CC=1.CO>[Cl:25][C:20]1[CH:19]=[C:18]([C@@H:12]2[O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:14][C@H:13]2[C:15]([O:17][CH3:26])=[O:16])[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 66975341(6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid

Product 1

HCID 866638664-tert-butyl 6-methyl (6R,7R)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4,6-dicarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a mixed solution of (6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid (0.82 g) in toluene (10 ml) and methanol (2 mL) was added trimethylsilyldiazomethane (1.576 mL, 2 mol/l hexane solution) at 0° C. and the mixture was stirred for 30 min. Acetic acid was added until the solution became colorless. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate and water. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (0.51 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7a057b0da6af43a19026b3f4308b5e4f
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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