p-Toluenesulfonic acid → 4-[(S)-2-Benzyloxycarbonylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionyl]-piperazine-1-carboxylic acid ethyl ester

HRID 1970497Notes

Reaction equation

HRID 1970497 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:30])[C@@H:13]([NH:19][C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:31]1(C)[CH:36]=CC(S(O)(=O)=O)=C[CH:32]=1.COC(OC)(C)C>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:30])[C@@H:13]([NH:19][C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:14][CH:15]2[CH2:16][O:17][C:31]([CH3:36])([CH3:32])[O:18]2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 668551894-((S)-2-Benzyloxycarbonylamino-4,5-dihydroxy-pentanoyl)-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 668547494-[(S)-2-Benzyloxycarbonylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionyl]-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 755 mg 4-((S)-2-Benzyloxycarbonylamino-4,5-dihydroxy-pentanoyl)-piperazine-1-carboxylic acid ethyl ester in 10 ml dichloromethane were added 10 mg p-toluenesulfonic acid and 10 ml 2,2-dimethoxypropane and the solution stirred for 1 h. The reaction mixture was concentrated, the residue dissolved in dichloromethane and washed with saturated aqueous NaHCO3 and brine. The crude product obtained after evaporation of the solvent was directly used in the next reaction step. Yield: 612 mg.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with saturated aqueous NaHCO3 and brine

Sources & evidence

ORD record
ord-82130c188d0b4ed69de48eb0cb0cc427
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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