Benzoyl isothiocyanate → HCID 90253577, compound

HRID 1478751Notes

Reaction equation

HRID 1478751 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@@:13]1([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])[CH2:18][O:17][C@@H:16]([C:19]2([CH3:22])[CH2:21][CH2:20]2)[CH2:15][C@H:14]1[CH2:23][OH:24]>ClCCl>[F:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[C@@:13]1([NH:12][C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[S:11])[C@H:14]([CH2:23][OH:24])[CH2:15][C@H:16]([C:19]2([CH3:22])[CH2:21][CH2:20]2)[O:17][CH2:18]1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 90253579HCID 90253579, compound

Product 1

HCID 90253577HCID 90253577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl isothiocyanate (0.98 g, 6.00 mmol) was added drop-wise to a solution of rel-[(2R,4R,5S)-5-amino-5-(2,4-difluorophenyl)-2-(1-methylcyclopropyl)tetrahydro-2H-pyran-4-yl]methanol (C58) (2.20 g, 5.00 mmol) in dichloromethane (60 mL). After the reaction mixture had stirred at room temperature for 15 hours, it was partitioned between aqueous hydrochloric acid (0.1 M, 20 mL) and dichloromethane (35 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (25 mL) and with saturated aqueous sodium chloride solution (25 mL), then dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 15% ethyl acetate in petroleum ether) provided the product as a brown solid. Yield: 1.1 g, 2.39 mmol, 48%.

Workup

  1. customit was partitioned between aqueous hydrochloric acid (0.1 M, 20 mL) and dichloromethane (35 mL)
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (25 mL) and with saturated aqueous sodium chloride solution (25 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (Gradient: 0% to 15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-1266c65fd0cf4c24bf059bd46974c102
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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