Acetic Acid → HCID 70510747, compound

HRID 1262894Notes

Reaction equation

HRID 1262894 reaction equation
C([O:8]C([NH:11][C@H:12]([C:28]([NH:30][C@@H:31]([C:34]([NH:36][CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:35])[CH2:32][OH:33])=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20]CC2C=CC=CC=2)=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.C(O)(=O)C>[Pd].CO>[OH2:8].[NH2:11][C@H:12]([C:28]([NH:30][C@@H:31]([C:34]([NH:36][CH2:37][CH2:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:35])[CH2:32][OH:33])=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 13419969HCID 13419969, compound

Product 1

HCID 70510747HCID 70510747, compoundYield 29.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-N-(3-phenylpropyl)-D-serinamide (1.25 g.), acetic acid (125 mg.) and palladium on carbon (10%, 100 mg.) in methanol (50 ml.) was hydrogenated under pressure for 30 hours, then filtered. The filtrate was stripped of volatiles. The residue was purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel (350 g.) using ammonium acetate (0.2%) in methanol-water (1:1) as the eluant, and an aqueous solution of the product was lyophilized, affording as an amorphous white solid L-tyrosyl-N-(3-phenylpropyl)-D-serinamide hydrate (3:2) (245 mg.; [α]D25 +16.9°, c=1, methanol), whose unsolvated form is the compound of Formula II wherein Q is Ser, R1, R2 and R5 are each hydrogen and R4 is (CH2)nY wherein n is 3 and Y is phenyl.

Workup

  1. filtrationfiltered
  2. customThe residue was purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel (350 g.)

Sources & evidence

ORD record
ord-2c21146f56cd4d36bef88f9290cccf55
Source dataset
uspto-grants-1984_06
Patent number
US04454120

Reaction notes

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