p-Toluenesulfonic acid → HCID 54514706, compound

HRID 2165224Notes

Reaction equation

HRID 2165224 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:27]([O:29][CH2:30][C@@H:31]([C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[NH:32][C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])=[O:28])[CH:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:14]C1CCCCO1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:27]([O:29][CH2:30][C@@H:31]([C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[NH:32][C:33](=[O:38])[C:34]([F:37])([F:35])[F:36])=[O:28])[CH:13]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18639969HCID 18639969, compound

Product 1

HCID 54514706HCID 54514706, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl O-(N-benzyloxycarbonyl-3-phenyl-O-tetrahydropyranyl-D,L-serinyl)-N-trifluoroacetyl-L-serinate (0.8 g) in methanol (10 ml) was added p-toluenesulfonic acid (45.6 mg) at room temperature. After stirring for an hour at room temperature, the reaction mixture was concentrated and the residue was chromatographed on preparative thin layer chromatography to give benzyl O-(N-benzyloxycarbonyl-3-phenyl-D,L-serinyl)-N-trifluoroacetyl-L-serinate (404 mg).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was chromatographed on preparative thin layer chromatography

Sources & evidence

ORD record
ord-bc5f342fa8d442f2a63ede4cc213b7b6
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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