Acetic Acid → Methyl 4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate

HRID 28221

Reaction equation

HRID 28221 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][C:5]1([CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][S:15][CH:14]2[CH2:19][CH2:20][CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(O)(=O)C>CCOCC>[OH:4][C:5]1([CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][S:15][CH:14]2[CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:3])=[O:27])=[CH:29][CH:30]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 1750274-(3-((2-(1-Hydroxycyclohexyl)ethyl)-4-oxo-2-thiazolidinyl)propyl)benzoic acid

Product 1

HCID 13174084Methyl 4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (approximately 2.5 g., 0.06 mole) in ether (100 ml.) is mixed with a solution of 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (11.7 g., 0.03 mole) in ether (100 ml.). The resulting solution is allowed to stand at room temperature for 6 hours. Acetic acid is then added to destroy the excess diazomethane, and the solution is washed with dilute sodium bicarbonate solution and dried over sodium sulfate. Evaporation of volatile materials in vacuo yields the title compound as a nearly colorless, viscous oil.

Workup

  1. customto destroy the excess diazomethane
  2. washthe solution is washed with dilute sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of volatile materials in vacuo

Sources & evidence

ORD record
ord-b9da721fd1b54c3ab4a2f599d27dc867
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Linked notes

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