Hydrochloric Acid → HCID 15671502, compound

HRID 2371410Notes

Reaction equation

HRID 2371410 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[CH2:24]I)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl.[C:30]([O:37][CH3:38])(=[O:36])[CH2:31][C:32]([O:34][CH3:35])=[O:33]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[CH2:24][CH:31]([C:30]([O:37][CH3:38])=[O:36])[C:32]([O:34][CH3:35])=[O:33])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 15671511HCID 15671511, compound

Product 1

HCID 15671502HCID 15671502, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-iodomethyl-4-t-butyldimethylsilyloxypyrrolidine (100 g) in dry dimethylformamide (500 ml), dimethyl malonate (43.16 ml) and 28% (w/w) methanolic solution of sodium methoxide (60.77 g) were added, and the resultant mixture was stirred at room temperature for 2 days. The reaction mixture was neutralized with 1N hydrochloric acid, diluted with ethyl acetate, washed with water and dried over magnesium sulfate. Removal of the solvent gave (2R,4R)-1-benzyloxycarbonyl-2-(2,2-dimethoxycarbonylethyl)-4-t-butyldimethylsiloxypyrrolidine.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-6d5d422900214686a92348306b7cf062
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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