tert-Butyl isothiocyanate → N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(3-carboxybenzyl)ethyl]thiourea

HRID 47724

Reaction equation

HRID 47724 reaction equation
Cl.[NH2:2][C@H:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([OH:15])=[O:14])[CH:8]=1)[CH2:4][OH:5].[C:16]([N:20]=[C:21]=[S:22])([CH3:19])([CH3:18])[CH3:17]>C(O)C.C(N(CC)CC)C>[C:16]([NH:20][C:21]([NH:2][C@H:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([OH:15])=[O:14])[CH:8]=1)[CH2:4][OH:5])=[S:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 11544tert-Butyl isothiocyanateHCID 69885138(2R)-2-amino-3-(3-carboxyphenyl)-1-propanol hydrochloride

Product 1

HCID 86584425N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(3-carboxybenzyl)ethyl]thiourea

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

The process is performed as in Example 2, starting with 1.82 g of (2R)-2-amino-3-(3-carboxyphenyl)-1-propanol hydrochloride in 20 cm3 of ethanol, 4.2 cm3 of triethylamine and 1.7 cm3 of tert-butyl isothiocyanate. After heating for 21 hours at a temperature in the region of 60° C. and an identical work-up, 2.31 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(3-carboxybenzyl)ethyl]thiourea are obtained in the form of a light brown foam. (Rf=0.33 in a 12/6/1 by volume mixture of chloroform/methanol/aqueous ammonia, on a Merck 60F254R silica plate).

Sources & evidence

ORD record
ord-f5a7dae54b1446baa90c25675b969057
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Linked notes

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