4-Methylmorpholine → N-t-butoxycarbonyl-L-tyrosylglycylglycine benzyl ester

HRID 372772Notes

Reaction equation

HRID 372772 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:17])[CH2:11][NH:12][C:13](=[O:16])[CH2:14][NH2:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ClC1C(Cl)=CC(Cl)=CC=1[O:27][C:28](=O)[C@H:29]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1)[NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].CN1CCOCC1>C(Cl)Cl>[CH2:2]([O:9][C:10](=[O:17])[CH2:11][NH:12][C:13](=[O:16])[CH2:14][NH:15][C:28](=[O:27])[C@H:29]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1)[NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 13996146Glycyl-glycine benzyl ester hydrochlorideHCID 54469426N-t-butoxycarbonyl-L-tyrosine 2,3,5-trichlorophenyl ester

Product 1

HCID 10624762N-t-butoxycarbonyl-L-tyrosylglycylglycine benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.4 parts glycylglycine benzyl ester hydrochloride, 9.1 parts N-t-butoxycarbonyl-L-tyrosine 2,3,5-trichlorophenyl ester and 1.8 parts N-methylmorpholine in 150 parts methylene chloride is stirred overnight at room temperature. The solvent is then removed by evaporation under reduced pressure. The crude material is subjected to low-pressure column chromatography on silica gel to afford N-t-butoxycarbonyl-L-tyrosylglycylglycine benzyl ester.

Workup

  1. customThe solvent is then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-52d5a1b262c64ca1b274c4f94cea28ae
Source dataset
uspto-grants-1978_05
Patent number
US04092304

Reaction notes

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