Water → HCID 59711084, compound

HRID 493446Notes

Reaction equation

HRID 493446 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)[CH3:2].[CH2:13]([NH:20][C:21](=[O:42])[CH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[O:29][C:28]([CH3:34])([CH3:33])[CH:27]([OH:35])[CH:26]2[NH:36][CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.O>ClCCl>[CH2:13]([NH:20][C:21](=[O:42])[CH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[O:29][C:28]([CH3:34])([CH3:33])[CH:27]([OH:35])[CH:26]2[N:36]([S:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5709594-Ethylbenzene-1-sulfonyl chlorideHCID 69054048HCID 69054048, compound

Product 1

HCID 59711084HCID 59711084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

4.1 ml 4-ethyl benzenesulfonyl chloride was added dropwise to a solution of 10.8 g of the N-benzyl-2-[3-hydroxy-2,2-dimethyl-4-(neopentylamino)-3,4-dihydro-2H-chromen-6-yl]acetamide obtained above in Example 3 and 5 ml triethylamine in 100 ml dichloromethane. Dichloromethane was immediately substantially completely evaporated at reduced pressure, and the resulting reaction mixture was stirred for 90 minutes at 65° C. and 180 bar. The entire batch was poured into 150 ml water, and the aqueous phase was extracted once with 200 ml ethyl acetate. The solvent was largely evaporated at reduced pressure, the remaining residue was dried over sodium sulfate, and the remaining residue was chromatographed on silica gel (mobile phase: petroleum ether/ethyl acetate 3:1 v/v). Drying the product fractions in an oil pump vacuum yielded 3.6 g of the title compound (2 conformers) as colorless oil.

Workup

  1. customDichloromethane was immediately substantially completely evaporated at reduced pressure
  2. customthe resulting reaction mixture
  3. extractionthe aqueous phase was extracted once with 200 ml ethyl acetate
  4. customThe solvent was largely evaporated at reduced pressure
  5. dry with materialthe remaining residue was dried over sodium sulfate
  6. customthe remaining residue was chromatographed on silica gel (mobile phase: petroleum ether/ethyl acetate 3:1 v/v)
  7. customDrying the product fractions in an oil pump vacuum

Sources & evidence

ORD record
ord-01eb3325e0214dbc82f35c7b0bc71cde
Source dataset
uspto-grants-2009_05
Patent number
US07534903B2

Reaction notes

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