HCID 13419961, compound → HCID 86739486, compound

HRID 1262889Notes

Reaction equation

HRID 1262889 reaction equation
C(OC([NH:8][C@H:9]([C:22]([N:24]([CH3:42])[C@@H:25]([C:30]([NH:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:31])[CH2:26][CH2:27][S:28][CH3:29])=[O:23])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]C(C)(C)C)=[CH:13][CH:12]=1)=O)(C)(C)C.C(OCC)(=O)C.[ClH:49]>>[ClH:49].[NH2:8][C@H:9]([C:22]([N:24]([CH3:42])[C@@H:25]([C:30]([NH:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:31])[CH2:26][CH2:27][S:28][CH3:29])=[O:23])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 13419961HCID 13419961, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 86739486HCID 86739486, compound

Procedure

A solution of [N-(tert-butyloxycarbonyl)-O-(tert-butyl)-L-tyrosyl]-N2 -methyl-N-(3-phenylpropyl)-D-methioninamide (1.81 g.) in hydrogen chloride-ethyl acetate (3.4 N, 20 ml.) was stirred for one hour at room temperature, then stripped of volatiles. The product was crystallized from isopropyl alcohol, affording L-tyrosyl-N2 -methyl-N-(3-phenylpropyl)-D-methioninamide monohydrochloride (966 mg.; m.r. 208°-210° C.; [α]D25 +85.7°, c=1, methanol), whose free base is the compound of Formula II wherein Q is Met, R1 and R5 are each hydrogen, R2 is methyl and R4 is (CH2)nY wherein n is 3 and Y is phenyl.

Workup

  1. customThe product was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-5dd81e91a9014bb6a06ace65e298f403
Source dataset
uspto-grants-1984_06
Patent number
US04454120

Reaction notes

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