Ethanol → HCID 178467767, compound

HRID 1613495Notes

Reaction equation

HRID 1613495 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([C:20]2([CH2:25][CH:26]([CH2:30][CH2:31][O:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1.C(O)C.O.[OH-].[Na+]>O1CCOCC1>[C:9]([C@@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([C:20]2([CH2:25][CH:26]([CH2:30][CH2:31][O:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[CH2:13][CH2:12]1)([OH:10])=[O:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 178467768HCID 178467768, compound

Product 1

HCID 178467767HCID 178467767, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-{1-[(cis-4-Benzyloxycarbonyl-cyclohexyl)carbamoyl]cyclopentyl}-2-(2-ethoxyethyl)propanoic acid (225 mg, 0.476 mmole) was dissolved in 1,4-dioxan (20 ml), ethanol (4 ml) and water (6 ml) and was treated with 1N sodium hydroxide solution (2.4 ml, 2.4 mmole). After 20 hours at room temperature, the solution was evaporated to half volume, diluted with water (20 ml) and washed with diethyl ether. The aqueous layer was separated, acidified with 2N hydrochloric acid and extracted with ethyl acetate (3×20 ml). The ethyl acetate layer was separated, dried over magnesium sulphate and the solvent evaporated to give the title product as a colourless foam (161 mg, 88%). Found: C,61.89; H,8.29; N,3.62. C20H33NO6,0.2 H2O requires C,62.06; H,8.69; N,3.62%.

Workup

  1. customthe solution was evaporated to half volume
  2. additiondiluted with water (20 ml)
  3. washwashed with diethyl ether
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate (3×20 ml)
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried over magnesium sulphate
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-84715f6ac7fa40429433966e0ace3a90
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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