1-Propene, 3-methoxy- → ((4S)-2,2-dimethyl-3-t-butoxycarbonyl-4-(2-methylpropyl)-1,3-oxazolidin-5-yl)carboxylic Acid Methyl Ester

HRID 857084Notes

Reaction equation

HRID 857084 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([OH:19])[C@@H:5]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH:7]([CH3:10])[CH2:8]C.CO[CH2:23][CH:24]=[CH2:25]>CN(C)C=O>[CH3:1][O:2][C:3]([CH:4]1[O:19][C:24]([CH3:25])([CH3:23])[N:11]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[C@H:5]1[CH2:6][CH:7]([CH3:8])[CH3:10])=[O:20]

Participants

4

Reactant 2

HCID 693921-Propene, 3-methoxy-HCID 86589144(3S)-3-(N-t-butoxycarbonylamino)-5-methyl-2-hydroxyheptanoic acid methyl ester

Product 1

HCID 58760363((4S)-2,2-dimethyl-3-t-butoxycarbonyl-4-(2-methylpropyl)-1,3-oxazolidin-5-yl)carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3S)-3-(N-t-butoxycarbonylamino)-5-methyl-2-hydroxyheptanoic acid methyl ester (4.40 g) in N,N-dimethylformamide (16 ml) was added methyl-2-propenyl ether (4.60 ml) and further was added dl-camphor sulfonic acid (186 mg) and the mixture was stirred overnight at room temperature. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1 to 4:1) to give the title compound (3.90 g) having the following physical data.

Workup

  1. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1 to 4:1)

Sources & evidence

ORD record
ord-40674dfd1eb242b0b042d02d206755f8
Source dataset
uspto-grants-2006_12
Patent number
US07144901B2

Reaction notes

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