tert-Butyl isothiocyanate → N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(phenylmethyl)ethyl]thiourea

HRID 47722

Reaction equation

HRID 47722 reaction equation
[NH2:1][C@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][OH:4].[C:12]([N:16]=[C:17]=[S:18])([CH3:15])([CH3:14])[CH3:13]>C(O)C>[C:12]([NH:16][C:17]([NH:1][C@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][OH:4])=[S:18])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 11544tert-Butyl isothiocyanateHCID 853475phenylalaninol, (R)-

Product 1

HCID 86584424N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(phenylmethyl)ethyl]thioureaYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The process is performed as in Example 2, starting with 5 g of (R)-(+)2-amino-3-phenyl-1-propanol in 50 cm3 of ethanol and 5.7 g of tert-butyl isothiocyanate at a temperature in the region of 20° C. for 16 hours. After an identical work-up, 8.7 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(phenylmethyl)ethyl]thiourea are obtained in the form of a white solid melting at 107° C.

Sources & evidence

ORD record
ord-787673440b6549b1a89c1c97caa345fe
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Linked notes

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