Acetic Acid → HCID 68291874, compound

HRID 339827Notes

Reaction equation

HRID 339827 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][S:16]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([Li])C=CC=CC=1.[CH3:38][C:39]([CH3:41])=[O:40].C(O)(=O)C>C1COCC1.C(OCC)(=O)C>[CH3:30][O:29][C:22]1[CH:23]=[C:24]([O:27][CH3:28])[CH:25]=[CH:26][C:21]=1[CH2:20][NH:19][S:16]([CH:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1)[C:39]([OH:40])([CH3:41])[CH3:38])(=[O:18])=[O:17]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 68291850HCID 68291850, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 68291874HCID 68291874, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Under inert gas, 3.22 g of C-(4-benzyloxyphenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide were initially charged in 70 ml of THF, and then, at a temperature of −78° C., 12.50 ml of a 1.8 N phenyllithium solution were added dropwise. The reaction mixture was allowed to come to 0° C. and stirred briefly, then cooled again to −78° C., and 4.00 ml of acetone were added dropwise. The mixture was allowed to come to −20° C. within 15 minutes, admixed with 1.29 ml of acetic acid and 100 ml of ethyl acetate, and washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 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 (3.65 g) with a molecular weight of 485.6 g/mol (C26H31NO6S).

Workup

  1. customto come to 0° C.
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude product was purified by means of normal phase chromatography
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-bce811d864894255ae5b0b238ead6942
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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