Trifluoroacetic acid → (2S)-2-(Quinoline-8-sulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid

HRID 352671Notes

Reaction equation

HRID 352671 reaction equation
C([O:5][C:6](=[O:43])[C@@H:7]([NH:29][S:30]([C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:42]=1[N:41]=[CH:40][CH:39]=[CH:38]2)(=[O:32])=[O:31])[CH2:8][NH:9][C:10](=[O:28])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]2[NH:22][CH2:23][CH2:24][CH2:25][N:26]=2)=[CH:13][CH:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:41]1[C:42]2[C:37](=[CH:36][CH:35]=[CH:34][C:33]=2[S:30]([NH:29][C@@H:7]([CH2:8][NH:9][C:10](=[O:28])[C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]3[NH:22][CH2:23][CH2:24][CH2:25][N:26]=3)=[CH:15][CH:16]=2)[C:6]([OH:43])=[O:5])(=[O:31])=[O:32])[CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15550491(2S)-2-(quinoline-8-sulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid tert-butyl ester

Product 1

HCID 11649708(2S)-2-(Quinoline-8-sulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

72 mg (0.11 mmol) of (2S)-2-(quinoline-8-sulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid tert-butyl ester was dissolved in 2 ml of dichloromethane and 2 ml of trifluoroacetic acid was added. The solution was stirred at room temperature for 3 hours. The solvent was removed in vacuo and toluene was added to the residue and then removed in vacuo. The residue was dissolved in acetonitrile/water (1/1) and lyophilized. Yield 54 mg. MS (ES+): m/e=553 (M+H+).

Workup

  1. customThe solvent was removed in vacuo and toluene
  2. additionwas added to the residue
  3. customremoved in vacuo
  4. dissolutionThe residue was dissolved in acetonitrile/water (1/1)

Sources & evidence

ORD record
ord-e2f24a48bf9641d1bc65a7a4a390f74f
Source dataset
uspto-grants-2004_06
Patent number
US06747148B2

Reaction notes

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