tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(3-(4,5-dihydro-1H-imidazol-2-ylcarbamoyl)-propoxy)phenyl)propionate → (2S)-2-Benzyloxycarbonylamino-3-(4-(3-(4,5-dihydro-1H-imidazol-2-ylcarbamoyl)propyloxy)phenyl)propionic Acid

HRID 2297394Notes

Reaction equation

HRID 2297394 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][C:31](=[O:38])[NH:32][C:33]2[NH:34][CH2:35][CH2:36][N:37]=2)=[CH:23][CH:22]=1)[C:13]([O:15]C(C)(C)C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][C:31](=[O:38])[NH:32][C:33]2[NH:37][CH2:36][CH2:35][N:34]=2)=[CH:23][CH:22]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 11145802tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(3-(4,5-dihydro-1H-imidazol-2-ylcarbamoyl)-propoxy)phenyl)propionate

Product 1

HCID 11037987(2S)-2-Benzyloxycarbonylamino-3-(4-(3-(4,5-dihydro-1H-imidazol-2-ylcarbamoyl)propyloxy)phenyl)propionic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

200 mg of tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(3-(4,5-dihydro-1H-imidazol-2-ylcarbamoyl)-propoxy)phenyl)propionate were dissolved in 5 ml of trifluoroacetic acid/water (95/5) and the solution was stirred at room temperature for 15 min. The reaction solution was then concentrated in vacuo. The residue was dissolved in water and the solution was freeze-dried. Yield: 100%.

Workup

  1. concentrationThe reaction solution was then concentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. customthe solution was freeze-dried

Sources & evidence

ORD record
ord-b96b95b801d44fad92b3ad981dd79a81
Source dataset
uspto-grants-2002_12
Patent number
US06492356B1

Reaction notes

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