Water → HCID 68291848, compound

HRID 339828Notes

Reaction equation

HRID 339828 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH:10]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)[C:11]([OH:14])([CH3:13])[CH3:12])(=[O:9])=[O:8].FC(F)(F)C(O)=O.O.C(=O)([O-])O.[Na+]>ClCCl>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([CH:10]([S:7]([NH2:6])(=[O:9])=[O:8])[C:11]([OH:14])([CH3:13])[CH3:12])=[CH:16][CH:17]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 68291874HCID 68291874, compound

Product 1

HCID 68291848HCID 68291848, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.65 g of N-[2,4-dimethoxybenzyl]-1-(4-benzyloxyphenyl)-2-hydroxy-2-methylpropane-1-sulfonamide in 20 ml of dichloromethane was admixed with 4.00 ml of trifluoroacetic acid and stirred at room temperature for 20 minutes. The conversion was checked by LCMS. Since it was incomplete, another 2.00 ml of trifluoroacetic acid were added and the mixture was stirred for a further 2 hours. The reaction solution was admixed with 20 ml of water and neutralized with saturated aqueous sodium hydrogencarbonate solution. The precipitate was filtered off with suction through a glass frit, washed with dichloromethane and water and dried in a desiccator over P2O5. This gave the product (1.95 g) with a molecular weight of 335.4 g/mol (C17H21NO4S).

Workup

  1. stirringthe mixture was stirred for a further 2 hours
  2. filtrationThe precipitate was filtered off with suction through a glass frit
  3. washwashed with dichloromethane and water
  4. dry with materialdried in a desiccator over P2O5

Sources & evidence

ORD record
ord-40c140c05c7e414cae06f9b9bc13aec6
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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