HCID 22882481, compound → HCID 22882483, compound

HRID 863292Notes

Reaction equation

HRID 863292 reaction equation
[Na].[CH3:2][Si](C)(C)N[Si](C)(C)C.[C:11]([O:15][C:16]([N:18]1[C@@H:22]([CH2:23][C:24]2([CH:27]=O)[CH2:26][CH2:25]2)[CH2:21][O:20][C:19]1([CH3:30])[CH3:29])=[O:17])([CH3:14])([CH3:13])[CH3:12]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:11]([O:15][C:16]([N:18]1[C@@H:22]([CH2:23][C:24]2([CH:27]=[CH2:2])[CH2:25][CH2:26]2)[CH2:21][O:20][C:19]1([CH3:30])[CH3:29])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 22882481HCID 22882481, compoundHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 22882483HCID 22882483, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

27.05 g of sodium-hexamethyldisilazane are added in portions to a suspension of 52.7 g of methyltriphenylphosphonium bromide in 470 ml of tetrahydrofuran in the course of 10 min. 20.9 g of 3-tert-butoxycarbonyl-2,2-dimethyl-4(S)-[(1-formylcyclopropyl)methyl]-1,3-oxazolidine are added dropwise to this mixture at 5° C. in the course of 10 min, and after warming to room temperature, the mixture is stirred for 1 h. The mixture is poured onto ice-water and the aqueous phase is extracted with methylene chloride. The title compound is purified by means of FC over 900 g of silica gel (mobile phase G): Rf (G)=0.56.

Workup

  1. additionThe mixture is poured onto ice-water
  2. extractionthe aqueous phase is extracted with methylene chloride
  3. customThe title compound is purified by means of FC over 900 g of silica gel (mobile phase G)

Sources & evidence

ORD record
ord-93b7e8bbb3a94a55a687864783787c07
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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