Diethyl Ether → HCID 68914714, compound

HRID 870381Notes

Reaction equation

HRID 870381 reaction equation
[C:1]([O:5][C:6](=[O:34])[N:7]([C@H:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH:17]=2)[CH2:12]1)[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[CH3:35][Mg]Br.C(OCC)C>O1CCCC1>[C:1]([O:5][C:6](=[O:34])[N:7]([C@H:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([OH:33])([CH3:35])[CH3:32])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH:17]=2)[CH2:12]1)[CH2:8][CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 68912303HCID 68912303, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 68914714HCID 68914714, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[(S)-6-(4-Acetyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propyl-carbamic acid tert-butyl ester (400 mg, 0.71 mmol) was dissolved in tetrahydrofuran (15 ml) at 0° C. A 3 molar solution of methylmagnesium bromide in diethyl ether (2.82 ml, 7.12 mmol) was added slowly and the reaction mixture was stirred for 3 hours at room temperature. Another portion of a 3 molar solution of methylmagnesium bromide in diethyl ether (0.5 ml, 1.26 mmol) was added. Since no further conversion was observed, the reaction mixture was evaporated to dryness. Water (20 ml) was added to the residue and the aqueous phase was extracted with diethyl ether (50 ml) twice. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield the crude product. The crude product was purified by MPLC chromatography using dichloromethane/methanol (100:0-70:30) as eluent, yielding the product (300 mg, 47% purity, 39%).

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. additionWater (20 ml) was added to the residue
  3. extractionthe aqueous phase was extracted with diethyl ether (50 ml) twice
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-96f09feb65044845b6692d5c53b5fde8
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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