Lithium Hydroxide → 3-(Allyl-benzyloxycarbonyl-amino)-5-oxazol-2-yl-benzoic acid

HRID 1664213Notes

Reaction equation

HRID 1664213 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[C:6]([N:15]([CH2:26][CH:27]=[CH2:28])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH:5]=1.[Li+].[OH-]>CO.O.Cl.C(Cl)Cl>[CH2:26]([N:15]([C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=1)[C:3]([OH:29])=[O:2])[CH:27]=[CH2:28]

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 674411643-(Allyl-benzyloxycarbonyl-amino)-5-oxazol-2-yl-benzoic acid methyl ester

Product 1

HCID 674393183-(Allyl-benzyloxycarbonyl-amino)-5-oxazol-2-yl-benzoic acid

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-(Allyl-benzyloxycarbonyl-amino)-5-oxazol-2-yl-benzoic acid methyl ester (300 mg, 757 μmol, 1 eq) is dissolved in methanol (10 ml) and H2O (4 ml). LiOH*H2O (100 mg, 2.37 mmol, 3.13 eq) is added to the reaction mixture, which is stirred for 8 h at rt and then diluted with HCl (1N in H2O) and DCM. The combined organic solvents are separated and washed with brine, dried over sodium sulfate, filtered and concentrated. The resulting crystals are washed with hexane and dried under vacuum to give the product.

Workup

  1. customThe combined organic solvents are separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe resulting crystals are washed with hexane
  7. customdried under vacuum
  8. customto give the product

Sources & evidence

ORD record
ord-dd2c536962e14c3a9bb77a965e2c1af5
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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