tert-Butanol → 3-tert-butyl 2-diphenylmethyl (2RS,3RS)-5-oxotetrahydrofuran-2,3-dicarboxylate

HRID 2287493Notes

Reaction equation

HRID 2287493 reaction equation
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:8][C:9]([CH:11]2[CH:15]([C:16]([OH:18])=[O:17])[CH2:14][C:13](=[O:19])[O:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26](O)([CH3:29])([CH3:28])[CH3:27].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:19]=[C:13]1[O:12][CH:11]([C:9]([O:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:10])[CH:15]([C:16]([O:18][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:17])[CH2:14]1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18705268(2RS,3SR)-2-diphenylmethoxycarbonyl-5-oxotetrahydrofuran-3-carboxylic Acid

Product 1

HCID 538073673-tert-butyl 2-diphenylmethyl (2RS,3RS)-5-oxotetrahydrofuran-2,3-dicarboxylateYield 77.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

163 mg of (2RS,3SR)-2-diphenylmethoxycarbonyl-5-oxotetrahydrofuran-3-carboxylic acid, 59 mg of 4-dimethylaminopyridine and 36 mg of tert-butanol in 4 ml of methylene chloride were stirred with 110 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride at room temperature for 13 hours. The reaction solution was diluted with methylene chloride, washed successively with 10% aqueous citric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1] to give 148 mg of the title compound as a colorless oily substance.

Workup

  1. washwashed successively with 10% aqueous citric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1]

Sources & evidence

ORD record
ord-afdba351e3f44124be9445ef648fc085
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Reaction notes

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