Trifluoroacetic acid → 4-[2-(2-Aminothiazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine

HRID 583662Notes

Reaction equation

HRID 583662 reaction equation
[C:1]([O:5][C:6](=[O:37])[C@@H:7]([NH:27][S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH2:8][NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([NH2:25])[S:23][CH:24]=2)=[CH:13][CH:12]=1)(C)(C)[CH3:2].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=[O:46]>C(Cl)Cl>[CH2:1]([OH:5])[CH3:2].[NH4+:9].[OH-:46].[OH2:5].[NH2:25][C:22]1[S:23][CH:24]=[C:20]([CH2:19][CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]([C:10]([NH:9][CH2:8][C@H:7]([NH:27][S:28]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)(=[O:30])=[O:29])[C:6]([OH:37])=[O:5])=[O:26])=[CH:16][CH:15]=2)[N:21]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 158507274-[2-(2-Aminothiazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester

Product 2

HCID 158507284-[2-(2-Aminothiazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanineHCID 86596525Ethanol ammonium hydroxide water

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 5-5 (33 mg, 60 mmol), CH2Cl2 (0.5 mL), and triethylsilane (24 μL, 0.15 mmol) at ambient temperature was treated with TFA (0.5 mL). After 4 h, the solution was concentrated and the residual TFA removed azeotropically with toluene. Flash chromatography (silica, 10:0.1:0.1 ethanol/NH4OH/H2O) gave 5-6 as a white solid.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residual TFA removed azeotropically with toluene

Sources & evidence

ORD record
ord-ff1fc6610d9d4d72945d67c1332692c0
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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