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

HRID 488274Notes

Reaction equation

HRID 488274 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].S(Cl)(Cl)=O.[NH:36]([CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH2:37][C:38]([O:40][CH3:41])=[O:39]>>[CH3:46][O:45][C:43](=[O:44])[CH2:42][N:36]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:7](=[O:9])[C:6]1[CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 428827Methyl 2-[(2-methoxy-2-oxoethyl)amino]acetateHCID 193889433-Nitro-5-(octadecyloxy)benzoic acid

Product 1

HCID 19091793N-(2-methoxy-2-oxoethyl)-N-[3-nitro-5-(octadecyloxy)benzoyl]glycine methyl esterYield 79%

Procedure

Conversion of 3-nitro-5-(octadecyloxy)benzoic acid to the acid chloride with thionyl chloride followed by treatment with dimethyl iminodiacetate gave a 79% yield of N-(2-methoxy-2-oxoethyl)-N-[3-nitro-5-(octadecyloxy)benzoyl]glycine methyl ester as an oil after chromatography on silica gel using 25% ethyl acetate-hexane. The nmr spectrum was consistent with the structure.

Sources & evidence

ORD record
ord-b159704409d14b8095666a4585619db6
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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