HCID 131714101, compound → HCID 13575044, compound

HRID 279900Notes

Reaction equation

HRID 279900 reaction equation
[C:1]([CH2:4][CH2:5][C:6]([NH:8][C@H:9]([C:11]([N:13]1[CH2:27][CH2:26][CH2:25][C@H:14]1[C:15]([O:17]CC1C=CC=CC=1)=[O:16])=[O:12])[CH3:10])=[O:7])([OH:3])=[O:2]>C(O)C.[Pd]>[C:1]([CH2:4][CH2:5][C:6]([NH:8][C@H:9]([C:11]([N:13]1[CH2:27][CH2:26][CH2:25][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])[CH3:10])=[O:7])([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 131714101HCID 131714101, compound

Product 1

HCID 13575044HCID 13575044, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the phenylmethyl ester product from part (a) (700 mg., 1.86 mmole) in 95% ethanol (100 ml.) containing 10% palladium on carbon catalyst (100 mg.) is hydrogenated at 25 psi in a Parr apparatus for 19 hours, after which it is filtered and concentrated to give 1-[N-(3-carboxy-1-oxopropyl)-L-alanyl]-L-proline as a colorless oil. This diacid product is dissolved in water, passed through a column of AG 50 W X8 (Li+) and lyophilized to give 1-[N-(3-carboxy-1-oxopropyl)-L-alanyl]-L-proline, dilithium salt as a stable, off white solid which is homogeneous by TLC (Rf 0.6, silica gel, 3:1:1 n-butanol:acetic acid: water). [α]D =-100° (1.5% water).

Workup

  1. filtrationafter which it is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ad7870dc98d545208e7185fcd4572b47
Source dataset
uspto-grants-1986_05
Patent number
US04587234

Reaction notes

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