tert-Butyl isothiocyanate → ethyl (2R)-5-{[(benzyloxy)carbonyl]amino}-2-(3-tert-butylthioureido)pentanoate

HRID 47773Notes

Reaction equation

[C:1]([N:5]=[C:6]=[S:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:9][C@H:10]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[CH2:23]([O:22][C:20]([NH:19][CH2:18][CH2:17][CH2:16][C@@H:10]([NH:9][C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[S:7])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 20 °C

Procedure

7.5 cm3 of tert-butyl isothiocyanate are added to a solution of 13 g of ethyl (2R)-2-amino-5-[(benzyloxy)carbonyl]amino-pentanoate hydrochloride in 200 cm3 of ethanol, and the mixture is then stirred at a temperature in the region of 20° C. After 48 hours, the reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C. to give 16 g of ethyl (2R)-5-{[(benzyloxy)carbonyl]amino}-2-(3-tert-butyl-thioureido)pentanoate in the form of a colorless oil [mass spectrum: EI m/z=409 M+ m/z=232 (C13H14NO3)+ m/z=142 (232-PhCH)+ m/z=91 (C7H7)+].

Workup

concentrationthe reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C.

Sources & evidence

ORD record: ord-06682c65eab24b52ae0b03d47cc37b33
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699895B2

Reaction notes

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