Dicyclohexylcarbodiimide → 3-(N-octanoylglycylglycyloxy)octadecanoic acid tert-butyl ester

HRID 1249218Notes

Reaction equation

HRID 1249218 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][CH:8]([OH:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH3:4])([CH3:3])[CH3:2].[C:26]([NH:35][CH2:36][C:37]([NH:39][CH2:40][C:41](O)=[O:42])=[O:38])(=[O:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[CH2:7][CH:8]([O:24][C:41](=[O:42])[CH2:40][NH:39][C:37](=[O:38])[CH2:36][NH:35][C:26](=[O:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 312837N-octanoylglycylglycineHCID 13962663Tert-butyl 3-hydroxyoctadecanoate

Product 1

HCID 544231263-(N-octanoylglycylglycyloxy)octadecanoic acid tert-butyl esterYield 29.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.96 g of 3-hydroxyoctadecanoic acid tert-butyl ester and 1.43 g of N-octanoylglycylglycine were mixed with 40 ml of methylenechloride. By following the same procedure as in Example 23-(i) after adding 60 mg of DMAP and 1.14 g of DCC, 970 mg of 3-(N-octanoylglycylglycyloxy)octadecanoic acid tert-butyl ester was obtained.

Sources & evidence

ORD record
ord-e852c88a226c46ac94471dd9c594483b
Source dataset
uspto-grants-1986_12
Patent number
US04629736

Reaction notes

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