Water → 2-Cyclohexylethylaminophenylacetic acid

HRID 128330Notes

Reaction equation

HRID 128330 reaction equation
[CH:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=C[C:13]([CH2:16][C:17](O)=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:20].[Na+].I[CH2:23]C(O)CO.CN(C)P(N(C)C)(N(C)C)=O.[OH2:39]>CCOCC>[CH:1]1([CH2:7][CH2:8][NH:9][CH:10]([C:11]2[CH:12]=[CH:13][CH:16]=[CH:17][CH:23]=2)[C:15]([OH:39])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 962WaterHCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 921273-Iodo-1,2-propanediolHCID 204989854-(2-Cyclohexylethylamino)phenylacetic acid

Product 1

HCID 803996532-Cyclohexylethylaminophenylacetic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.34 g. of 4-(2-cyclohexylethylamino)-phenylacetic 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-(2-cyclohexylethylaminophenylacetic acid.

Workup

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

Sources & evidence

ORD record
ord-9d0834c108e3489eaa5e62aae7f8d83c
Source dataset
uspto-grants-1981_03
Patent number
US04259352

Reaction notes

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