Sodium Hydroxide → (4R,5E)-4-tert-butoxycarbonylamino-7-oxo-8-(3,5-dimethylphenyl)oct-5-enoic acid ethyl ester

HRID 853836Notes

Reaction equation

HRID 853836 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1)[CH2:5]P(=O)(OC)OC.[C:21]([O:25][C:26]([NH:28][C@@H:29]([CH:37]=O)[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:27])([CH3:24])([CH3:23])[CH3:22].[OH-].[Na+]>O1CCCC1.O.C(OC)(C)(C)C>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][CH2:30][C@@H:29]([NH:28][C:26]([O:25][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:27])/[CH:37]=[CH:5]/[C:4](=[O:3])[CH2:12][C:13]1[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)[CH3:36]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 57894011ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoateHCID 71389878Dimethyl [3-(3,5-dimethylphenyl)-2-oxopropyl]phosphonate

Product 1

HCID 69238228(4R,5E)-4-tert-butoxycarbonylamino-7-oxo-8-(3,5-dimethylphenyl)oct-5-enoic acid ethyl esterYield 64.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

Under atmosphere of argon, a suspension of 60% sodium hydride (50 mg) was added by a solution of dimethyl (2-oxo-3-(3,5-dimethylphenyl)propyl)phosphonate (373 mg) in tetrahydrofuran (5 mL) at the temperature of 0° C. The mixture was stirred for an hour and then a solution of ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoate (298 mg) in tetrahydrofuran (5 mL) was added to the mixture. The mixture was stirred for an hour. To the mixture, metyl tert-butyl ether and water were added, and then 1N a solution of sodium hydroxide was added. The organic layer was washed with saturated brine, dried over an anhydrous magnesium sulfate, concentrated and was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to give the title compound (300 mg) having the following physical data.

Workup

  1. stirringThe mixture was stirred for an hour
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over an anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customwas purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-e3560ee567e04209b146bba385980e9b
Source dataset
uspto-grants-2007_08
Patent number
US07256211B1

Reaction notes

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