Methanol → HCID 18713369, compound

HRID 279055Notes

Reaction equation

HRID 279055 reaction equation
C([Li])CCC.C(O)(C)(C)C.[CH2:11]([O:13][C:14]([NH:16][C:17]1[CH:37]=[CH:36][C:20]([C:21]([C:23]2[N:24]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:25]=[CH:26][CH:27]=2)=[O:22])=[CH:19][CH:18]=1)=[O:15])[CH3:12].[CH3:38][OH:39]>C1COCC1>[OH:39][CH2:38][C@@H:11]1[O:13][C:14](=[O:15])[N:16]([C:17]2[CH:37]=[CH:36][C:20]([C:21]([C:23]3[N:24]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:25]=[CH:26][CH:27]=3)=[O:22])=[CH:19][CH:18]=2)[CH2:12]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6386tert-ButanolHCID 22624265HCID 22624265, compoundHCID 178418339Butyllithium

Product 1

HCID 18713369HCID 18713369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyl lithium (4.6 ml. of 1.6 M solution in THF, 7.36 mM) was added to a stirred solution of t-butanol (0.505 g) in dry THF at −20° C. under nitrogen and the mixture stirred for 20 minutes. The temperature was lowered to −60° C. and 2-(4-ethoxycarbonylaminobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole (2.2 g. 5.67 mM) added over 15 minutes. The mixture was stirred for 50 minutes and a solution of R-(−) glycidyl butyrate (0.9 g. 6.25 mM) in dry THF (5 ml) added. The mixture was allowed to warm to ambient temperature and stirred for 24 hours. MeOH (20 ml) was added and the solution evaporated and the residue partitioned between EtOAc and water The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using 2% MeOH/dichloromethane as eluant, to give 5(R)-hydroxymethyl-N-(4-[1-(2-trimethylsilylethoxymethyl)pyrrol-2-ylcarbonyl]phenyl)oxazolidin-2-one as an oil (0.77 g; MS: 417 (MM−)).

Workup

  1. customwas lowered to −60° C.
  2. stirringThe mixture was stirred for 50 minutes
  3. stirringstirred for 24 hours
  4. customthe solution evaporated
  5. customthe residue partitioned between EtOAc and water The organic layer
  6. washwas washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a3bc09b7dfc54e0ca1a01e9bfd5702f2
Source dataset
uspto-grants-2002_03
Patent number
US06362191B1

Reaction notes

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