1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → Carbamic acid, (1-cyanocyclopropyl)-, 1,1-dimethylethyl ester (9CI)

HRID 1040430

Reaction equation

HRID 1040430 reaction equation
OCCC(NO)=N.ONC(=N)CC.FC(F)(F)CC(NO)=N.[C:23]([O:27][C:28](=[O:37])[NH:29][C:30]1([C:33](=N)[NH:34]O)[CH2:32][CH2:31]1)([CH3:26])([CH3:25])[CH3:24].C(OC(NC1(C(O)=O)CC1)=O)(C)(C)C>>[C:23]([O:27][C:28](=[O:37])[NH:29][C:30]1([C:33]#[N:34])[CH2:32][CH2:31]1)([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 5

HCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 178452922[1-(N-Hydroxy-carbamimidoyl)-cyclopropyl]-carbamic acid tert-butyl esterHCID 178458070HCID 178458070, compoundHCID 178511070HCID 178511070, compoundHCID 178511200HCID 178511200, compound

Product 1

HCID 20825555Carbamic acid, (1-cyanocyclopropyl)-, 1,1-dimethylethyl ester (9CI)

Procedure

The following compounds were prepared using similar procedures as described above: 3,N-Dihydroxy-propionamidine, N-Hydroxy-propionamidine, 3,3,3-Trifluoro-N-hydroxy-propionamidine, N-Hydroxy-dimethylamine-1-carboxamidine, [1-(N-Hydroxy-carbamimidoyl)-cyclopropyl]-carbamic acid tert-butyl ester; (1-Cyano-cyclopropyl)-carbamic acid tert-butyl ester was prepared from 1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid according to literature procedures (Demko, Z. P.; Sharpless, K. B. Org. Lett. 2002, 4, 2525).

Workup

  1. customThe following compounds were prepared

Sources & evidence

ORD record
ord-ab3ce088ae114c7b892d7bfb681fbaa2
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Linked notes

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