Dichloromethane → (4R)-3-[(2R,3S,4R,5S,6S,7Z)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-1-oxo-7,9-decadienyl]4-(phenylmethyl)-2-oxazolidinone

HRID 857966Notes

Reaction equation

HRID 857966 reaction equation
[OH:1][C@@H:2]([C@H:20]([CH3:38])[C@@H:21]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C@@H:22]([CH3:27])/[CH:23]=[CH:24]\[CH:25]=[CH2:26])[C@@H:3]([CH3:19])[C:4]([N:6]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][O:8][C:7]1=[O:18])=[O:5].N1C(C)=CC=CC=1C.C(Cl)Cl.[Si:50](OS(C(F)(F)F)(=O)=O)([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51]>CCOCC>[CH3:54][C:53]([Si:50]([CH3:52])([CH3:51])[O:1][C@@H:2]([C@H:20]([CH3:38])[C@@H:21]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)[C@@H:22]([CH3:27])/[CH:23]=[CH:24]\[CH:25]=[CH2:26])[C@@H:3]([CH3:19])[C:4]([N:6]1[C@H:10]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:9][O:8][C:7]1=[O:18])=[O:5])([CH3:56])[CH3:55]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 86760329(4R)-3-[(2R,3S,4S,5S,6S,7Z)-3-hydroxy-5-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-1-oxo-7,9-decadienyl]-4-(phenylmethyl)-2-oxazolidinone

Product 1

HCID 87896690(4R)-3-[(2R,3S,4R,5S,6S,7Z)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-1-oxo-7,9-decadienyl]4-(phenylmethyl)-2-oxazolidinoneYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (4R)-3-[(2R,3S,4S,5S,6S,7Z)-3-hydroxy-5-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-1-oxo-7,9-decadienyl]-4-(phenylmethyl)-2-oxazolidinone (3.4 g, 6.53 mmol), 2,6-lutidine (3.5 g, 32.65 mmol) and methylene chloride (100 mL) is cooled to 0° C. TBSOTf (7.12 g, 26.94 mmol)is added over 30 min and the resultant mixture is allowed to react overnight at 0° C. The mixture is diluted with ether (300 mL), washed with aqueous NaHSO4, brine, and concentrated. Flash chromatography affords the desired compound (3.6 g, 87%) as an oil.

Workup

  1. customto react overnight at 0° C
  2. washwashed with aqueous NaHSO4, brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-667006b13d8a4da882482444e6331677
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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