Benzaldehyde → N-tert-butyloxycarbonyl-1-(hydroxyphenylmethyl)cyclopropanesulfonamide

HRID 2369944Notes

Reaction equation

HRID 2369944 reaction equation
[C:1]([O:5][C:6]([NH:8][S:9]([CH:12]1[CH2:14][CH2:13]1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.CCCCCC.[Cl-].[NH4+]>[C:1]([O:5][C:6]([NH:8][S:9]([C:12]1([CH:20]([OH:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:14]1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 20773763tert-Butyl (cyclopropanesulfonyl)carbamateHCID 178418339Butyllithium

Product 1

HCID 68353399N-tert-butyloxycarbonyl-1-(hydroxyphenylmethyl)cyclopropanesulfonamide

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

Under inert gas, 1.00 g of N-tert-butyloxycarbonylcyclopropanesulfonamide were initially charged in 40 ml of THF, and then, at a temperature of −78° C., 6.63 ml of a 1.5 N butyllithium solution in hexane were added dropwise and the mixture was left to stir while cooling with ice for 1 hour. After stirring at room temperature for a further 30 minutes, the mixture was cooled again to −78° C., and a solution of 0.92 ml of benzaldehyde in 4 ml of THF was added. The mixture was allowed to come to room temperature while stirring overnight. The reaction solution was diluted with 20 ml of a saturated aqueous ammonium chloride solution and extracted with 40 ml of ethyl acetate, and the organic phase was dried over Na2SO4 and concentrated by rotary evaporation. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (880 mg) with a molecular weight of 327.4 g/mol (C15H21NO5S); MS (ESI): m/e=254 (M-tert-butanol+H+).

Workup

  1. waitthe mixture was left
  2. temperaturewhile cooling with ice for 1 hour
  3. stirringAfter stirring at room temperature for a further 30 minutes
  4. customto come to room temperature
  5. stirringwhile stirring overnight
  6. extractionextracted with 40 ml of ethyl acetate
  7. dry with materialthe organic phase was dried over Na2SO4
  8. concentrationconcentrated by rotary evaporation
  9. customThe crude product was purified by means of normal phase chromatography
  10. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-1dde643a2d544368a0af5d94a8c240ab
Source dataset
uspto-grants-2014_04
Patent number
US08710050B2

Reaction notes

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