Benzoyl isothiocyanate → HCID 90253444, compound

HRID 1478762Notes

Reaction equation

HRID 1478762 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]([CH2:19][CH:20]2[CH2:22][CH2:21]2)[CH2:15][C@H:14]1[CH2:23][OH:24]>ClCCl>[CH:20]1([CH2:19][C@@H:16]2[O:17][CH2:18][C@@:13]([NH:12][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[S:11])([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])[C@H:14]([CH2:23][OH:24])[CH2:15]2)[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 90253458HCID 90253458, compound

Product 1

HCID 90253444HCID 90253444, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl isothiocyanate (0.6 g, 3.7 mmol) was added drop-wise to a solution of rel-[(2S,4R,5S)-5-amino-2-(cyclopropylmethyl)-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol (C71) (1.10 g, 3.7 mmol) in dichloromethane (30 mL). After the reaction mixture had stirred at room temperature for 15 hours, it was concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in petroleum ether) provided the product as a brown solid. Yield: 1.14 g, 2.47 mmol, 67%. LCMS m/z 461 [M+H+].

Workup

  1. concentrationit was concentrated in vacuo
  2. customPurification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-0deb68cfe9cd4ccb9981eb7a8729fdd7
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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