Benzoyl isothiocyanate → HCID 58102219, compound

HRID 2060785Notes

Reaction equation

HRID 2060785 reaction equation
[NH2:1][C:2]1([C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH2:6][CH:5]([O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])[CH2:4][CH:3]1[CH2:15][OH:16].[C:31]([N:39]=[C:40]=[S:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[Si:8]([O:7][CH:5]1[CH2:6][C:2]([NH:1][C:40]([NH:39][C:31](=[O:38])[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[S:41])([C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH:3]([CH2:15][OH:16])[CH2:4]1)([C:11]([CH3:13])([CH3:12])[CH3:14])([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 57504913HCID 57504913, compound

Product 1

HCID 58102219HCID 58102219, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-amino-4-(tert-butyldimethylsilyloxy)-2-(3′-methoxybiphenyl-3-yl)cyclopentyl)methanol (9.44 g, 22.1 mmol) and benzoyl isothiocyanate (3.49 g, 21.0 mmol) in THF (88 mL) is stirred for 1.5 hours at room temperature and concentrated under reduced pressure. The crude product is purified by silica gel chromatography eluting with a linear gradient of 0% to 5% methanol in dichloromethane over 27 minutes to give the title compound (9.61 g, 70%). ES/MS m/e: 589 (M−1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product is purified by silica gel chromatography
  3. washeluting with a linear gradient of 0% to 5% methanol in dichloromethane over 27 minutes

Sources & evidence

ORD record
ord-f80533a96c6c48e5894ffc1517f14152
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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