Phenol → HCID 86585048, compound

HRID 1264396Notes

Reaction equation

HRID 1264396 reaction equation
C([O:3][C:4](=[O:45])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:44])[CH2:13][N:14]([C:16]([C@@H:18]2[CH2:22][C@@H:21]([S:23]CC3C=CC(OC)=CC=3)[CH2:20][N:19]2[S:33]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:35])=[O:34])=[O:17])[CH3:15])=[CH:7][CH:6]=1)C.[Li+].[OH-].COC1C=CC(CS[C@H]2CN(S(CCC3C=CC=CC=3)(=O)=O)[C@H](C(N(C)CC(NC3C=CC(C(O)=O)=CC=3)=O)=O)C2)=CC=1.C1(O)C=CC=CC=1>C(O)(C(F)(F)F)=O>[SH:23][C@H:21]1[CH2:20][N:19]([S:33]([CH2:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)(=[O:34])=[O:35])[C@H:18]([C:16]([N:14]([CH3:15])[CH2:13][C:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:45])=[O:3])=[CH:6][CH:7]=2)=[O:44])=[O:17])[CH2:22]1

Participants

6

Reactant 4

HCID 996PhenolHCID 3939Lithium HydroxideHCID 70004461HCID 70004461, compoundHCID 70005206HCID 70005206, compound

Product 1

HCID 86585048HCID 86585048, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

157 mg (0.24 mmol) (2S,4R)-4-(2-{[4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino}-acetylamino)-benzoic acid ethyl ester were treated with 0.1 M LiOH according to 5.2., the crude product (2S,4R)-4-(2-{[4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino}-acetylamino)-benzoic acid was dissolved in 1 ml TFA and heated to 75° C. in the presence of 23 mg (0.24 mmol) phenol for 1.5 h. The solvent was evaporated, the oil dissolved in toluene and evaporated (twice), the residue was titurated from hexane to yield 45 mg (2S,4R)-4-[2-[[4-Mercapto-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino]-acetylamino]-benzoic acid as light yellow solid, MS: 506 (MH+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe oil dissolved in toluene
  3. customevaporated (twice), the residue

Sources & evidence

ORD record
ord-c9ba68420bbd4208af0a62fee39b40a5
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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