Hydrochloric Acid → HCID 13933336, compound

HRID 652351Notes

Reaction equation

HRID 652351 reaction equation
C(OC([NH:8][C@@H:9]([CH2:41][CH:42]([CH3:44])[CH3:43])[CH:10]([OH:40])[CH2:11][NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:25]([NH:27][C@H:28]([C:36]([O:38][CH3:39])=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=O)(C)(C)C.[ClH:45].O>C(OCC)(=O)C>[ClH:45].[ClH:45].[NH2:8][C@@H:9]([CH2:41][CH:42]([CH3:44])[CH3:43])[CH:10]([OH:40])[CH2:11][NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:25]([NH:27][C@H:28]([C:36]([O:38][CH3:39])=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])[CH2:14][CH:15]([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 131714423HCID 131714423, compound

Product 1

HCID 13933336HCID 13933336, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 250 mg of N-[N-[N-[(3S)-3-[[(t-butyloxy)carbonyl]amino]-2-hydroxy-5-methylhexyl]-L-leucyl]-L-valyl]-L-phenylalanine, methyl ester (faster isomer) in 3 ml of ethyl acetate was cooled in an ice bath under nitrogen then treated with anhydrous hydrogen chloride gas to saturation. Once the reaction was saturated, the ice bath was removed, the reaction was stoppered, and stirred at ambient temperature. After one hour, the reaction was concentrated to dryness in vacuo, then recrystallized from methanol/ether at room temperature, and refrigerated overnight to afford 155 mg of the title compound as a hydrate with 1.0 mole of water, melting point 220°-223° C., dec.

Workup

  1. customthe ice bath was removed
  2. concentrationthe reaction was concentrated to dryness in vacuo
  3. customrecrystallized from methanol/ether at room temperature

Sources & evidence

ORD record
ord-11c9f712e5404f7a802818d8796908db
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

Loading…