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

HRID 443674Notes

Reaction equation

HRID 443674 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-af0e41fa61b043d981243ec7ab85110a
Source dataset
uspto-grants-1981_04
Patent number
US04260771

Reaction notes

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