Methanol → HCID 178456013, compound

HRID 1655725Notes

Reaction equation

HRID 1655725 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18][C:19]([C@@H:21]([NH:28][C:29]([C@H:31]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:32][C:33]([N:35]2[CH2:40][CH2:39][CH:38]([C:41]([O:43]CC)=[O:42])[CH2:37][CH2:36]2)=[O:34])=[O:30])[CH2:22][C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)=[O:20])[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=[CH2:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.O>[OH-].[Na+]>[CH:1]1([CH2:7][C@H:8]([NH:18][C:19]([C@@H:21]([NH:28][C:29]([C@H:31]([CH2:46][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:32][C:33]([N:35]2[CH2:40][CH2:39][CH:38]([C:41]([OH:43])=[O:42])[CH2:37][CH2:36]2)=[O:34])=[O:30])[CH2:22][C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)=[O:20])[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:15])[CH3:16])[CH:12]=[CH2:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 178456014HCID 178456014, compound

Product 1

HCID 178456013HCID 178456013, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

70 mg (0.1 mmol) of ethyl 1-[(R)-3-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]-4-phenylbutyryl]-4-piperidinecarboxylate were suspended in 1N sodium hydroxide solution in a 9:1 mixture of methanol and water and stirred at room temperature for 3 hours. Thereafter, the solvent was evaporated and the residue was recrystallized from methanol/methylene chloride/hexane, to obtain 1-[(R)-3-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]-4-phenylbutyryl]-4-piperidinecarboxylic acid as white crystals, melting point 169°.

Workup

  1. customThereafter, the solvent was evaporated
  2. customthe residue was recrystallized from methanol/methylene chloride/hexane

Sources & evidence

ORD record
ord-2b2b74fd48e444ff88f17afe30f93913
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

Loading…