2,2-Dimethoxypropane → HCID 11066282, compound

HRID 1620762Notes

Reaction equation

HRID 1620762 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:21](OC)([CH3:23])[CH3:22].CC1C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O>[CH3:22][C:21]1([CH3:23])[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C@@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][O:14]1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11821096N-Z-D-serine methyl ester

Product 1

HCID 11066282HCID 11066282, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl N-[(benzyloxy)carbonyl]-D-serinate (1013 mg) and 2,2-dimethoxypropane (4166 mg) in acetone (20 mL) was added pyridin-1-ium 4-methylbenzenesulfonate (201 mg) at room temperature, and the reaction mixture was stirred at 60° C. overnight. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (860 mg).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a1fef624f5714ae49f84e15e42af1fe0
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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