Hexamethylphosphoramide → 2,3-Dihydroxypropyl 4-(15-carbomethoxypentadecylamino)benzoate

HRID 904253Notes

Reaction equation

HRID 904253 reaction equation
[C:1]([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][CH2:18][CH2:19][NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)([O:3][CH3:4])=[O:2].[OH-].[Na+].I[CH2:33][CH:34]([OH:37])[CH2:35][OH:36].CN(C)P(N(C)C)(N(C)C)=O>O.CCOCC>[C:1]([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][CH2:18][CH2:19][NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:33][CH:34]([OH:37])[CH2:35][OH:36])=[O:26])=[CH:28][CH:29]=1)([O:3][CH3:4])=[O:2]

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 921273-Iodo-1,2-propanediolHCID 12898273p-(15-Carbomethoxypentadecylamino)benzoic acid

Product 1

HCID 211632452,3-Dihydroxypropyl 4-(15-carbomethoxypentadecylamino)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.34 g. of 4-(15-carbomethoxypentadecylamino)benzoic acid, 4.80 g. of 25% aqueous sodium hydroxide, and 12.6 g. of 3-iodo-1,2-propanediol in 50 ml. of hexamethylphosphoramide is stirred for 24 hours at ambient temperature, diluted with 100 ml. of ether and stirred for 5 days at ambient temperature. The mixture is treated with water and extracted with ether. The dried extracts are evaporated to yield 2,3-dihydroxypropyl 4-(15-carbomethoxypentadecylamino)benzoate.

Workup

  1. additiondiluted with 100 ml
  2. extractionextracted with ether
  3. customThe dried extracts are evaporated

Sources & evidence

ORD record
ord-528112f10d68462b989291ea5f4a8a6c
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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