HCID 13419940, compound → HCID 70511677, compound

HRID 1262877Notes

Reaction equation

HRID 1262877 reaction equation
C([O:5]C([NH:8][C@H:9]([C:22]([NH:24][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.[ClH:42].O1CCOCC1>>[OH2:5].[ClH:42].[NH2:8][C@H:9]([C:22]([NH:24][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 13419940HCID 13419940, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 70511677HCID 70511677, compound

Procedure

A solution of [N-(tert-butyloxycarbonyl)-O-(tert-butyl)-L-tyrosyl]-N-(3-phenylpropyl)-D-methioninamide (610 mg.) in hydrogen chloride-dioxane (3.9 N, 10 ml.) was stirred at room temperature for 40 minutes, then concentrated under vacuum. Ether was added to the residue, the solution was concentrated under vacuum, and the process was repeated. A solution of the residue (502 mg.) in water (20 ml.) was filtered and lyophilized, affording as an amorphous off-white solid L-tyrosyl-N-(3-phenylpropyl)-D-methioninamide monohydrochloride monohydrate (473 mg.), whose free base is the compound of Formula II wherein Q is Met, R1, R2 and R5 are each hydrogen and R4 is (CH2)nY wherein n is 3 and Y is phenyl.

Workup

  1. concentrationconcentrated under vacuum
  2. additionEther was added to the residue
  3. concentrationthe solution was concentrated under vacuum
  4. filtrationA solution of the residue (502 mg.) in water (20 ml.) was filtered

Sources & evidence

ORD record
ord-45d185fde1714d61acb94320d6dfddcc
Source dataset
uspto-grants-1984_06
Patent number
US04454120

Reaction notes

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