4-Methylmorpholine → HCID 2063345, compound

HRID 1586651Notes

Reaction equation

HRID 1586651 reaction equation
CN1CCOCC1.[NH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].[NH:14]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:15]([C:23](O)=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[NH:14]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:15]([C:23]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 69221Glycine methyl esterHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 2063345HCID 2063345, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.01 g of N-methylmorpholine is added to a solution in 60 ml of methylene dichloride of 6.39 g of H-Phe-Gly-AHCP-Ile-AMPA [obtainable by subjecting H-Gly-OMe to a condensation reaction with BOC-Phe-OH to give BOC-Phe-Gly-OMe, saponifying the latter and subjecting the product to a condensation reaction with H-AHCP-Ile-AMPA to give BOC-Phe-Gly-AHCP-Ile-AMPA and splitting off the BOC group]. 2.43 g of 4-BOC-aminocyclohexanecarbonylic acid, 1.35 g of HOBt and a solution of 2.06 g of DCCI in 50 ml of methylene dichloride are added with stirring, the mixture is stirred for 14 hours at 0°-10°, the precipitated dicyclohexylurea is filtered off and the manner gives 4-BOC-aminocyclohexylcarbonyl-Phe-Gly-AHCP-Ile-AMPA, m.p. 141°-143°.

Sources & evidence

ORD record
ord-e9641faa3eb64a92a9777b34296b8eeb
Source dataset
uspto-grants-1993_06
Patent number
US05215967

Reaction notes

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