Hydrochloric Acid → HCID 131713675, compound

HRID 2417867Notes

Reaction equation

HRID 2417867 reaction equation
[C:1]([NH:9][CH:10]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:11](=[O:36])[CH2:12][N:13](C(OCC1C=CC=CC=1)=O)[C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:44]>C(O)C.[C].[Pd].CO>[ClH:44].[C:1]([NH:9][CH:10]([CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:11](=[O:36])[CH2:12][NH:13][C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 14127420HCID 14127420, compound

Product 1

HCID 131713675HCID 131713675, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

1-[N-[3-(Benzoylamino)-2-oxo-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, phneylmethyl ester (1.0 g.) is dissolved in absolute ethanol (30 ml.) and 1N hydrochloric acid (2.25 ml.). Palladium-carbon catalyst (10%, 200 mg.) is added and the solution is stirred under an atmosphere of hydrogen overnight. The catalyst is filtered off and the solution is evaporated. The crude product (700 mg.) is combined with 300 mg. of crude product from a previous small scale reaction and passed through a column of LH-20 (1 inch×15 inch) in methanol. The fractions containing the desired product are pooled, evaporated, dissolved in water and filtered. The clear aqueous solution is lyophilized to give 800 mg. of 1-[N-[3-(benzoylamino)-2-oxo-4-phenylbutyl]-L-alanyl]-L-proline, monohydrochloride; [α]D25 =-59.6 (c=1.4, methanol); m.p. 98°-130° (dec.). Tlc (silica gel, n-butanol/acetic acid/water, 4:1:1) Rf =0.44.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solution is evaporated
  3. customof crude product from a previous small scale reaction

Sources & evidence

ORD record
ord-611fff1692c04df7a5115c2f8b0479d0
Source dataset
uspto-grants-1984_09
Patent number
US04470973

Reaction notes

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