Trifluoroacetic acid → EtOAc EtOH H2O NH4OH

HRID 580908Notes

Reaction equation

HRID 580908 reaction equation
[C:1]([O:5][C:6](=[O:38])[C@@H:7]([NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH2:8][NH:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:27]=[CH:26][C:25]3[CH2:24][CH2:23][CH2:22][NH:21][C:20]=3[N:19]=2)[CH2:14][CH2:13]1)=[O:11])(C)(C)[CH3:2].[C:39](O)([C:41](F)(F)F)=[O:40]>C(Cl)Cl>[CH3:2][CH2:1][O:5][C:6]([CH3:7])=[O:38].[CH3:41][CH2:39][OH:40].[NH4+:9].[OH-:5].[OH2:5].[N:19]1[C:20]2[NH:21][CH2:22][CH2:23][CH2:24][C:25]=2[CH:26]=[CH:27][C:18]=1[CH:15]1[CH2:14][CH2:13][N:12]([C:10]([NH:9][CH2:8][C@H:7]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:30])=[O:31])[C:6]([OH:38])=[O:5])=[O:11])[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867541524-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)piperidin-1-yl-carbonyl-2-(S)-phenylsulfonylamino-beta-alanine t-butyl ester

Product 2

HCID 86752451EtOAc EtOH H2O NH4OHHCID 867541544-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)piperidin-1-yl-carbonyl-2-(S)-phenylsulfonylamino-beta-alanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ester 3-7 (60 mg, 0.1106 mmol), TFA (2 ml) and CH2Cl2 (2 ml) was stirred for 2.0 h. The reaction solution was concentrated and then azeotroped with toluene. Flash chromatography (silica, 25:10:1:1 AE 15:10:1:1 EtOAc/EtOH/NH4OH/H2O) gave acid 3-8 as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-635a836aa0a14d49a659ffa3f0518d82
Source dataset
uspto-grants-1999_07
Patent number
US05919792

Reaction notes

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