Sodium Hydroxide → HCID 9907375, compound

HRID 916678Notes

Reaction equation

HRID 916678 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C@@H:11]1/[CH:17]=[CH:18]/[C@@H:19]([OH:25])[CH2:20][CH2:21][CH:22]1[CH2:24][CH2:23]1.[OH-].[Na+]>CO>[CH:22]1([CH2:21][CH2:20][C@H:19]([OH:25])/[CH:18]=[CH:17]/[C@H:11]2[CH2:12][CH2:13][CH2:14][C:15](=[O:16])[N:10]2[CH2:9][CH2:8][S:7][CH2:6][CH2:5][CH2:4][C:3]([OH:26])=[O:2])[CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69246464HCID 69246464, compound

Product 1

HCID 9907375HCID 9907375, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A methanol (10 mL) solution of 4-{2-[(R)-2-((S)-(E)-5-Cyclopropyl-3-hydroxy-pent-1-enyl)-6-oxo-piperidin-1-yl]-ethylsulfanyl}-butyric acid methyl ester from step (4, 98 mg, 0.25 mmol) was treated with sodium hydroxide (0.3 mL, 5 M aqueous) and stirred at ambient temperature for 3 hours. The volatiles were removed under a stream of nitrogen and the mixture was partitioned between water and ethyl ether. The aqueous layer was rendered acidic with hydrochloric acid (12 M aqueous) and extracted with ethyl acetate (3×15 mL). The combined organic extracts was stored over anhydrous sodium sulfate. 4-{2-[(R)-2-((S)-(E)-5-Cyclopropyl-3-hydroxy-pent-1-enyl)-6-oxo-piperidin-1-yl]-ethylsulfanyl}-butyric acid (94 mg, 0.25 mmol) was obtained following filtration and removal of the volatiles as an oil: 1H NMR (300 MHz, CDCl3) δ 6.7 (br.s, 1 H), 5.58-5.63 (m, 2 H), 4.18-4.22 (m, 1 H), 4.02-4.07 (m, 1 H), 3.87-3.98 (m, 1 H), 2.98-3.08 (m, 1 H), 2.62-2.72 (m, 2 H), 2.59 (t, J=6.9 Hz, 2 H), 2.36-2.49 (m, 4 H), 1.61-1.99 (m, 8 H), 1.22-1.30 (m, 2 H), 0.59-0.71 (m, 1 H), 0.40-0.46 (m, 2 H), 0.00-0.06 (m, 2 H); MS: m/z M+1, 370.

Workup

  1. customThe volatiles were removed under a stream of nitrogen
  2. customthe mixture was partitioned between water and ethyl ether
  3. extractionextracted with ethyl acetate (3×15 mL)

Sources & evidence

ORD record
ord-ca2b44b4501a45b0b549c4480c7ec063
Source dataset
uspto-grants-2007_09
Patent number
US07271183B2

Reaction notes

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