Thionyl Chloride → N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)-5-(phenylmethoxy)benzoyl]glycine methyl ester

HRID 488269Notes

Reaction equation

HRID 488269 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=1)[C:23]([OH:25])=O)[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][CH2:16][CH2:17][CH3:18].S(Cl)(Cl)=O.[NH:41]([CH2:47][C:48]([O:50][CH3:51])=[O:49])[CH2:42][C:43]([O:45][CH3:46])=[O:44]>>[CH3:51][O:50][C:48](=[O:49])[CH2:47][N:41]([CH2:42][C:43]([O:45][CH3:46])=[O:44])[C:23](=[O:25])[C:22]1[CH:26]=[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[C:20]([O:19][CH2:1][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][CH2:16][CH2:17][CH3:18])[CH:21]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 428827Methyl 2-[(2-methoxy-2-oxoethyl)amino]acetateHCID 193890463-(Octadecyloxy)-5-(phenylmethoxy)benzoic acid

Product 1

HCID 19091826N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)-5-(phenylmethoxy)benzoyl]glycine methyl ester

Procedure

Conversion of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid to the acid chloride with thionyl chloride followed by treatment with dimethyl iminodiacetate gave N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)-5-(phenylmethoxy)benzoyl]glycine methyl ester as an oil after chromatography on 50 g of silica gel using 25% ethyl acetate-hexane. The structure was confirmed by the nmr spectrum.

Sources & evidence

ORD record
ord-a640b00347b44a50a9d126925ce2722f
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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