Potassium Carbonate → HCID 67054613, compound

HRID 490069Notes

Reaction equation

HRID 490069 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:30][CH:29]=2)([CH2:13][O:14]C(=O)C2C=CC=CC=2[N+]([O-])=O)[CH2:11][O:10][C:9]1([CH3:43])[CH3:42])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO.C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:12]([CH2:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:32][CH:33]=2)([CH2:13][OH:14])[CH2:11][O:10][C:9]1([CH3:43])[CH3:42])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67054623HCID 67054623, compound

Product 1

HCID 67054613HCID 67054613, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-(4-benzyloxy-phenyl)-ethyl]-2,2-dimethyl-4-(2-nitro-benzoyloxymethyl)-oxazolidine-3-carboxylic acid tert-butyl ester (80 mg, 0.13 mmol) in methanol (1 ml) and THF (1 ml) is added K2CO3 (1.5 mg, 0.076 eq), the reaction mixture is stirred overnight at room temperature. The reaction mixture is concentrated to dryness and 4-[2-(4-benzyloxy-phenyl)-ethyl]-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (51 mg, 85%) is isolated as a white solid after flash chromatography (Ethyl acetate/Hexane (1/4)).

Workup

  1. concentrationThe reaction mixture is concentrated to dryness

Sources & evidence

ORD record
ord-e730deec6b04425fbbdeee2dcb321a6a
Source dataset
uspto-grants-2009_05
Patent number
US07528120B2

Reaction notes

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