Hydrochloric Acid → N-[N-[(3S)-3-Amino-2-hydroxybutyl]-L-phenylalanvl]-L-leucine, dihydrochloride

HRID 1583678Notes

Reaction equation

HRID 1583678 reaction equation
C(OC([NH:8][C@@H:9]([CH3:37])[CH:10]([OH:36])[CH2:11][NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:29]([O:31]C(C)(C)C)=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:38]>C(O)(=O)C>[ClH:38].[ClH:38].[NH2:8][C@@H:9]([CH3:37])[CH:10]([OH:36])[CH2:11][NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:29]([OH:31])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13933328N-[(3S)-3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxybutyl]-L-phenylalanyl-L-leucine, t-butyl ester

Product 1

HCID 131714412N-[N-[(3S)-3-Amino-2-hydroxybutyl]-L-phenylalanvl]-L-leucine, dihydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-[N-[(3S)-3-[[(t-butyloxy)carbonyl]amino]-2-hydroxybutyl]-L-phenylalanyl-L-leucine, t-butyl ester (slower isomer) (0.27 g, 0.52 mmol) in 20 ml of 1.3N hydrogen chloride in acetic acid was allowed to stir for 2 hours at room temperature, during which time a white precipitate separated. The mixture was concentrated under reduced pressure to approximately one third of the original volume, then diluted with ether and filtered yielding 185 mg of the title compound as a white solid, melting point 236°-239° C. (with slow decomposition >210° C.). Analysis by 400 MHz 1H-NMR revealed the presence of a small amount (<5%) of the faster isomer.

Workup

  1. customseparated
  2. concentrationThe mixture was concentrated under reduced pressure to approximately one third of the original volume
  3. additiondiluted with ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-2b10a40f12114b3a95a6cd1697407ae5
Source dataset
uspto-grants-1985_11
Patent number
US04552866

Reaction notes

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