Lithium Hydroxide → HCID 86585068, compound

HRID 1264413Notes

Reaction equation

HRID 1264413 reaction equation
C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:12](=[O:42])[CH2:13][N:14]([C:16]([C@@H:18]2[CH2:22][C@@H:21]([S:23]C(=O)C)[CH2:20][N:19]2[S:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:32][CH:31]=2)(=[O:29])=[O:28])=[O:17])[CH3:15])[CH3:11])=[CH:6][CH:5]=1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C1COCC1>[C:33]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:32]=[CH:31][C:30]([S:27]([N:19]2[CH2:20][C@H:21]([SH:23])[CH2:22][C@H:18]2[C:16]([N:14]([CH2:13][C:12]([N:10]([CH3:11])[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:43])=[O:2])=[CH:5][CH:6]=2)=[O:42])[CH3:15])=[O:17])(=[O:28])=[O:29])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 86585069HCID 86585069, compound

Product 1

HCID 86585068HCID 86585068, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 106 mg (0.17 mmol) (2S,4R)-4-[[[[4-Acetylsulfanyl-1-(biphenyl-4-sulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino]-acetyl]-methyl-amino]-benzoic acid methyl ester in 10 ml THF were added 10 ml 0.1 M LiOH at 0° C. and the solution was stirred at RT for 2 h, poured on 2 ml 1M KHSO4 and extracted with EtOAc. The combined organic layers were washed with brine and were dried with Na2SO4. The residue was titrurated with hexane to give 67 mg (69%) (2S,4R)-4-[[[[1-(Biphenyl-4-sulfonyl)-4-mercapto-pyrrolidine-2-carbonyl]-methyl-amino]-acetyl]-methyl-amino]-benzoic acid as white solid, MS: 568 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialwere dried with Na2SO4

Sources & evidence

ORD record
ord-4692f8c981e640c789403edddca7afda
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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