HCID 53718425, compound → HCID 54333676, compound

HRID 1584408Notes

Reaction equation

HRID 1584408 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:13]([NH:15][O:16]C(C)(C)C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:21][S:22]([C:25]1[CH:26]=[CH:27][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:29][CH:30]=1)(=[O:23])=[O:24])[C:13]([NH:15][OH:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 53718425HCID 53718425, compound

Product 1

HCID 54333676HCID 54333676, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-2-(benzyloxycarbonylamino)-N-tert-butoxy-3-(4-phenoxyphenylsulfonyl)-propionamide (1.2 g) obtained from Example 16 in methylene chloride (5 ml) was diluted with trifluoroacetic acid (30 ml). The solution was allowed to stand overnight, and solvent was removed under reduced pressure. This residue was chromatographed on silica gel, eluting with 10% methanol/methylene chloride to give (R)-2-(benzyloxycarbonylamino)-N-hydroxy-3-(4-phenoxyphenylsulfonyl)-propionamide (400 mg), m.p. 195-202° C.

Workup

  1. customsolvent was removed under reduced pressure
  2. customThis residue was chromatographed on silica gel
  3. washeluting with 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-82e992d443684cf49304482b970a1c52
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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