HCID 70485509, compound → HCID 70485452, compound

HRID 484774Notes

Reaction equation

HRID 484774 reaction equation
C(OC([NH:8][C@H:9]([C:22]([NH:24][C@@H:25]([C:27]([N:29]([CH2:39][CH2:40][CH2:41][S:42][CH3:43])[CH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:28])[CH3:26])=[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>Cl.O1CCOCC1>[NH2:8][C@H:9]([C:22]([NH:24][C@@H:25]([C:27]([N:29]([CH2:39][CH2:40][CH2:41][S:42][CH3:43])[CH2:30][CH2:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:28])[CH3:26])=[O:23])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 70485509HCID 70485509, compound

Product 1

HCID 70485452HCID 70485452, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of N-(tert-butyloxycarbonyl)-O-(tert-butyl)-L-tyrosyl-N-[3-(methylthio)propyl]-N-(3-phenylpropyl)-D-alaninamide (2.42 g.) in hydrogen chloride-dioxane (3.9N, 50 ml.) was stirred for one and one half hours at room temperature, then stripped of volatiles under vacuum. The residue was triturated with ether, the solution was stripped of volatiles under vacuum, and the process was repeated. An aqueous solution of the residue was lyophilized. A solution of the residue in methanol (50 ml.) was stripped of volatiles, affording a white foam (1.960 g.). Part (950 mg.) of the white foam was twice more lyophilized, affording as an amorphous white solid L-tyrosyl-N-[3-(methylthio)propyl]-N-(3-phenylpropyl)-D-alaninamide monhydrochloride hemihydrate (675 mg.; [α]D25 +57.0, c=1, methanol), whose free base is the compound of Formula II wherein R2 is CHQ(CH2)nY wherein n is 2, Y is phenyl and Q is hydrogen and R3 is (CH2)mX wherein m is 3 and X is methylthio.

Workup

  1. customThe residue was triturated with ether
  2. customaffording a white foam (1.960 g.)

Sources & evidence

ORD record
ord-f627f2a16a514337ba512c27c82f576b
Source dataset
uspto-grants-1985_08
Patent number
US04533657

Reaction notes

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