Hydrochloric Acid → HCID 13933336, compound

HRID 652352Notes

Reaction equation

HRID 652352 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.[Cl:45]CCl.[ClH:48].O>C(OCC)(=O)C>[ClH:45].[ClH:48].[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 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 (slower isomer) (see example 6C) in 3 ml of ethyl acetate and 1.5 ml of dichloromethane was cooled in an ice bath under nitrogen, and 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, resuspended in 5 ml of ethyl acetate, cooled in an ice bath under nitrogen, resaturated with anhydrous hydrogen chloride and stoppered. After 30 minutes, the reaction was concentrated to dryness in vacuo, then recrystallized from methanol/ether at room temperature, and refrigerated overnight to afford 200 mg of the title compound as a hydrate with 0.4 mole of water, melting point 242°-252° C., dec. Analysis Calc'd. for C28H48N4O5.2HCl.0.4MH2O: C, 55.96; H, 8.52; N, 9.33; Cl, 11.80; Found: C, 55.96; H, 8.42; N, 9.31; Cl, 11.70.

Workup

  1. customthe ice bath was removed
  2. concentrationthe reaction was concentrated to dryness in vacuo
  3. temperaturecooled in an ice bath under nitrogen
  4. waitAfter 30 minutes
  5. concentrationthe reaction was concentrated to dryness in vacuo
  6. customrecrystallized from methanol/ether at room temperature

Sources & evidence

ORD record
ord-2b889ace115f46abb3891fb41221216f
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

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