tert-Butyl isothiocyanate → HCID 86675577, compound

HRID 1422586Notes

Reaction equation

[NH2:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)[CH2:4][CH:3]1[CH2:5][CH2:6][OH:7].[C:17]([N:21]=[C:22]=[S:23])([CH3:20])([CH3:19])[CH3:18]>C(#N)C>[C:17]([NH:21][C:22]([NH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)[CH2:4][CH:3]1[CH2:5][CH2:6][OH:7])=[S:23])([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-((1SR,2SR)-2-amino-2-(3-nitrophenyl)cyclopropyl)ethanol (intermediate A2c) (1.44 g, 6.48 mmol, Eq: 1.00) in dry acetonitrile (30 ml) was added at 23° C. tert-butyl isothiocyanate (1.12 g, 1.23 ml, 9.72 mmol, Eq: 1.5) and the mixture was stirred at 80° C. for 36 h. Evaporated to dryness and chromatography. The residue was chromatographed on 50 g SiO2 with 0-50% ethyl acetate in dichloromethane to give the 1-tert-butyl-3-((1SR,2SR)-2-(2-hydroxyethyl)-1-(3-nitrophenyl)cyclopropyl)thiourea (1.47 g, 4.36 mmol, 67.2% yield) as a light brown solid. MS (ISP): m/z=338.4 [(M+H)+].

Workup

customEvaporated to dryness and chromatography
customThe residue was chromatographed on 50 g SiO2 with 0-50% ethyl acetate in dichloromethane

Sources & evidence

ORD record: ord-30003833a0e74850bad090595097370c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927535B2

Reaction notes

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