Sodium Carbonate → 3-Benzyloxycarbonylamino-5-oxazol-2-yl-benzoic acid methyl ester

HRID 1664211Notes

Reaction equation

HRID 1664211 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[C:6]([NH2:15])[CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[C:6]([NH:15][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:5]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 674398663-Amino-5-oxazol-2-yl-benzoic acid methyl ester

Product 1

HCID 674415993-Benzyloxycarbonylamino-5-oxazol-2-yl-benzoic acid methyl ester

Procedure

A mixture of 10.3 g (47.2 mmol) of 3-amino-5-oxazol-2-yl-benzoic acid methyl ester, 25 g of anhydrous sodium carbonate and 7.69 ml (51.9 mmol) of benzyl chloroformate is stirred for 16 h at rt and filtered. The filtrate is concentrated, and the residue is chromatographed on silica gel (EtOAc/hexane 1:2) to yield the product in the form of colorless crystals.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated
  3. customthe residue is chromatographed on silica gel (EtOAc/hexane 1:2)
  4. customto yield the product in the form of colorless crystals

Sources & evidence

ORD record
ord-34973946517747248d11e023c8250a12
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

Loading…