Hydrochloric Acid → HCID 131714430, compound

HRID 1583695Notes

Reaction equation

HRID 1583695 reaction equation
C(OC([NH:8][C@@H:9]([CH2:37][CH:38]([CH3:40])[CH3:39])[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.CCOCC.[ClH:46]>C(O)(=O)C>[ClH:46].[NH2:8][C@@H:9]([CH2:37][CH:38]([CH3:40])[CH3:39])[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 131714431HCID 131714431, compound

Product 1

HCID 131714430HCID 131714430, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-[N-[(3S)-3-[[(t-butyloxy)carbonyl]amino]-2-hydroxy-5-methylhexyl]-L-phenylalanyl-L-leucine, t-butyl ester (845 mg, 1.5 mmol) in 22 ml of 1.3N hydrogen chloride in acetic acid was allowed to stir at room temperature for 2 hours. The resultant thick white slurry was evaporated to dryness in vacuo. The residue was dissolved in water and the solution was microfiltered and concentrated in vacuo to give a white gummy residue. Trituration with ether afforded 698 mg of the title compound as a fine white powder, melting point 179°-203° C. (with decomposition). The 13C-NMR spectrum was consistent with an approximately 2:1 mixture of alcohol isomers.

Workup

  1. customThe resultant thick white slurry was evaporated to dryness in vacuo
  2. dissolutionThe residue was dissolved in water
  3. concentrationconcentrated in vacuo
  4. customto give a white gummy residue

Sources & evidence

ORD record
ord-27c488e27fe74ffca3b2a56d39b709d0
Source dataset
uspto-grants-1985_11
Patent number
US04552866

Reaction notes

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