Acetic Anhydride → HCID 70027121, compound

HRID 398255Notes

Reaction equation

HRID 398255 reaction equation
[CH3:1][N:2]([C:27]([O:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:28])[C@@H:3]([C:24]([OH:26])=[O:25])[CH2:4][NH:5][C:6](=[O:23])[CH2:7][CH:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH2:22])=[N:20][OH:21])=[CH:15][CH:14]=2)[CH2:9]1.[C:34](OC(=O)C)(=O)[CH3:35]>C(O)(=O)C>[CH3:1][N:2]([C:27]([O:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:28])[C@@H:3]([C:24]([OH:26])=[O:25])[CH2:4][NH:5][C:6](=[O:23])[CH2:7][CH:8]1[O:12][N:11]=[C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[N:22]=[C:34]([CH3:35])[O:21][N:20]=3)=[CH:17][CH:18]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 136374407HCID 136374407, compound

Product 1

HCID 70027121HCID 70027121, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of (R)-Methyl-3-[[[3-[4-[amino(hydroxyimino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl]acetyl]amino]-N-(butoxycarbonyl)-L-alanine (1.05 g) in acetic acid (7 mL) was added acetic anhydride (0.35 g) dropwise. After the completion of addition, the reaction mixture was refluxed for 3 h. The solvent was distilled under vacuum and the solid was dried to give (R)-methyl-N-(butoxycarbonyl)-3-[[[4,5-dihydro-3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-5-isoxazolyl]acetyl]amino]-L-alanine (1.05 g).

Workup

  1. additionAfter the completion of addition
  2. temperaturethe reaction mixture was refluxed for 3 h
  3. distillationThe solvent was distilled under vacuum
  4. customthe solid was dried

Sources & evidence

ORD record
ord-7ff18fe2a0264fc3a303c527bee0c39c
Source dataset
uspto-grants-2003_08
Patent number
US06610858B2

Reaction notes

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