HCID 86754151, compound → HCID 15435122, compound

HRID 580876Notes

Reaction equation

HRID 580876 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:21](=[O:34])[CH2:22][O:23][NH:24][C:25](=[O:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:21](=[O:34])[CH2:22][O:23][NH:24][C:25](=[O:33])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:13][C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86754151HCID 86754151, compound

Product 1

HCID 15435122HCID 15435122, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Benzyloxycarbonylamino-4-oxo-5-phenylacetylaminooxy-pentanoic acid, 1,1 dimethylethyl ester (208 mg, 0.365 mmol) was taken up in 3 mL of 1:1 trifluoroacetic acid (TFA)CH2Cl2 and allowed to stir for 2 hours. Reaction was diluted with acetonitrile (MeCN) (10 mL) and concentrated. The residue was stripped down from MeCN five times. Purification by chromatography (SiO2, 90:9:1 CH2Cl2 -acetone-formic acid) afforded 3-benzyloxycarbonylamino-4-oxo-5-phenylacetylaminooxy-pentanoic acid (51 mg, 34%) as a white foam.

Workup

  1. customReaction
  2. concentrationconcentrated
  3. customPurification by chromatography (SiO2, 90:9:1 CH2Cl2 -acetone-formic acid)

Sources & evidence

ORD record
ord-e81b9f5ad76845d18c54b85a4b85b175
Source dataset
uspto-grants-1999_07
Patent number
US05919790

Reaction notes

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