tert-Butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-(4,5-dihydroimidazoi-2-ylcarbamoyl)propyloxy)phenyl)propionate → (2S)-2-(1-Adamantylmethyloxycarbonylamino)-3-(4-(3-(4,5-dihydroimidazol-2-ylcarbamoyl)propyloxy)phenyl)propionic Acid

HRID 1394015Notes

Reaction equation

HRID 1394015 reaction equation
[C:1]12([CH2:11][O:12][C:13]([NH:15][C@@H:16]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35](=[O:42])[NH:36][C:37]4[NH:38][CH2:39][CH2:40][N:41]=4)=[CH:27][CH:26]=3)[C:17]([O:19]C(C)(C)C)=[O:18])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>FC(F)(F)C(O)=O.O>[C:1]12([CH2:11][O:12][C:13]([NH:15][C@@H:16]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35](=[O:42])[NH:36][C:37]4[NH:41][CH2:40][CH2:39][N:38]=4)=[CH:29][CH:30]=3)[C:17]([OH:19])=[O:18])=[O:14])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

3

Reactant 1

HCID 67633290tert-Butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-(4,5-dihydroimidazoi-2-ylcarbamoyl)propyloxy)phenyl)propionate

Product 1

HCID 57027538(2S)-2-(1-Adamantylmethyloxycarbonylamino)-3-(4-(3-(4,5-dihydroimidazol-2-ylcarbamoyl)propyloxy)phenyl)propionic AcidYield 99.7%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

188 mg (0.32 mmol) of (5.1) were dissolved in 10 ml of trifluoroacetic acid/H2O (95:5). After 30 min, the solvent was removed in vacuo and the residue was digested with diisopropyl ether. After freeze-drying, 168 mg of an amorphous powder of (5.2) were obtained.

Workup

  1. customthe solvent was removed in vacuo
  2. customAfter freeze-drying

Sources & evidence

ORD record
ord-9a56a6af60fc42aeb8b078ad01b0a541
Source dataset
uspto-grants-2008_03
Patent number
US07348333B2

Reaction notes

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