Palmitoyl chloride → N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxohexadecylamino)benzoyl]glycine ethyl ester

HRID 488285Notes

Reaction equation

HRID 488285 reaction equation
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:19]([O:21][C:22](=[O:41])[CH2:23][N:24]([C:31](=[O:40])[C:32]1[CH:37]=[C:36]([NH2:38])[CH:35]=[C:34]([NH2:39])[CH:33]=1)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:20]>>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][N:24]([CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:41])[C:31](=[O:40])[C:32]1[CH:37]=[C:36]([NH:38][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:35]=[C:34]([NH:39][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:33]=1)[CH3:30]

Participants

3

Reactant 2

HCID 8206Palmitoyl chlorideHCID 19091775N-(3,5-diaminobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester

Product 1

HCID 19091838N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxohexadecylamino)benzoyl]glycine ethyl ester

Procedure

The reaction of palmitoyl chloride with N-(3,5-diaminobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester as in Example 54 gave N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxohexadecylamino)benzoyl]glycine ethyl ester as an oil after chromatography on silica gel using 35% ethyl acetate-hexane.

Sources & evidence

ORD record
ord-7223e8411b0a453fa879e8a191ae19ac
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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