Trifluoroacetic acid → 4-(2-Aminothiazol-4-yl)butanoyl-glycyl-2(S)-phenylsulfonamido-beta-alanine

HRID 618138Notes

Reaction equation

HRID 618138 reaction equation
C([O:5][C:6](=[O:35])[C@@H:7]([NH:25][S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH2:8][NH:9][C:10](=[O:24])[CH2:11][NH:12][C:13](=[O:23])[CH2:14][CH2:15][CH2:16][C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:22][C:19]1[S:20][CH:21]=[C:17]([CH2:16][CH2:15][CH2:14][C:13]([NH:12][CH2:11][C:10]([NH:9][CH2:8][C@H:7]([NH:25][S:26]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)(=[O:28])=[O:27])[C:6]([OH:35])=[O:5])=[O:24])=[O:23])[N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867544694-(2-Aminothiazol-4-yl)butanoyl-glycyl-2(S)-phenylsulfonamido-beta-alanine t-butyl ester

Product 1

HCID 158721494-(2-Aminothiazol-4-yl)butanoyl-glycyl-2(S)-phenylsulfonamido-beta-alanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ester 1-8 (365 mg, 0.69 mmol) was dissolved in CH2Cl2 (3.5 mL), then TFA (3.5 mL) was added. After 5 h the reaction mixture was concentrated, azeotroped with toluene, then purified by sequential flash chromatography (silica, 22:20:1:1 EtOAc/EtOH/H2O/NH4OH, then silica, 4:1:1 CH2Cl2 /MeOH/HOAc, then 7:1:1 CH2Cl2 /MeOH/HOAc), providing 1-9 as a white solid.

Workup

  1. concentrationAfter 5 h the reaction mixture was concentrated
  2. customazeotroped with toluene
  3. custompurified by sequential flash chromatography (silica, 22:20:1:1 EtOAc/EtOH/H2O/NH4OH

Sources & evidence

ORD record
ord-ffa263b8465b4c5aa4b3493a1720c837
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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