HCID 86759216, compound → HCID 70035103, compound

HRID 987932Notes

Reaction equation

HRID 987932 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21](OS(C)(=O)=O)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:10][C:9]1([CH3:34])[CH3:33])=[O:7])([CH3:4])([CH3:3])[CH3:2]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:10][C:9]1([CH3:33])[CH3:34])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 86759216HCID 86759216, compound

Product 1

HCID 70035103HCID 70035103, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-benzyl-5-(3-ethoxycarbonyl-2-methanesulfonyloxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (64 g) in dichloromethane (250 ml) was stirred at 15° C. under an atmosphere of nitrogen during the dropwise addition of 1,8-diazobicyclo[5,4,0]undec-7-ene (21.3ml). After 30 minutes, a further portion of 1,8-diazobicyclo[5,4,0]undec-7-ene (9.0ml) was added and the reaction mixture stirred for 1 hour. The solvent was evaporated and the residue dissolved in ethyl acetate, washed sequentially with 2M aqueous hydrochloric acid (500 ml and 250 ml), water, 5% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried (anhydrous magnesium sulfate) and evaporated to afford 4-benzyl-5-(3-ethoxycarbonyl-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (49 g, %) as an orange gum. Mass spectrum 404 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed sequentially with 2M aqueous hydrochloric acid (500 ml and 250 ml), water, 5% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-ee22c9ef2d084aa2ada6143f5593f25f
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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