Potassium bisulfate → benzyl N-[3-(2-aminoethyl)pyrrolidine-1-carboximidoyl]carbamate

HRID 1585494Notes

Reaction equation

C(OC([NH:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)=O)(C)(C)C.[CH2:16]([O:23][C:24]([NH:26][C:27](=[NH:30])SC)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1>[CH2:16]([O:23][C:24]([NH:26][C:27]([N:13]1[CH2:14][CH2:15][CH:11]([CH2:10][CH2:9][NH2:8])[CH2:12]1)=[NH:30])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 65 °C

Procedure

2.18 g (0.0102 mmole) (3RS)-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine and 2.81 g (0.0125 mole) N-benzyloxycarbonyl-S-methylisothiourea was dissolved in 30 ml toluene and heated to 60-70° C. for eight hours followed by stirring at room temperature for one day. 0.3 M KHSO4 -solution was added and the water layer was washed with a mixture of the toluene and ethyl acetate and left for 2 days under which time the Boc group was removed. The acidic water phase was made alkaline and extracted four times with CH2Cl2The combined organic layer was dried (Na2SO4), filtered and evaporated to yield 2.0 g (51%) of the title compound.

Workup

washthe water layer was washed with a mixture of the toluene and ethyl acetate
waitleft for 2 days under which time the Boc group
customwas removed
extractionextracted four times with CH2Cl2The combined organic layer
dry with materialwas dried (Na2SO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-998cc3bd3943482bad6d850e019abcfb
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05939392

Reaction notes

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