N-Acetyl-L-Cysteine → Tert-butyl 3-carbamimidoyl-3-(1,1-dimethylethylsulfinamido)azetidine-1-carboxylate

HRID 509557Notes

Reaction equation

C([NH:4][C@@H](CS)C(O)=O)(=O)C.[C:11]([C:13]1([NH:24][S:25]([C:27]([CH3:30])([CH3:29])[CH3:28])=[O:26])[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]1)#[N:12].C([O-])(=O)C.[NH4+]>CO>[C:11]([C:13]1([NH:24][S:25]([C:27]([CH3:30])([CH3:29])[CH3:28])=[O:26])[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH2:14]1)(=[NH:4])[NH2:12]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (R)-2-acetamido-3-mercaptopropanoic acid (N-acetylcycteine, 0.812 g, 4.98 mmol), tert-butyl 3-cyano-3-(1,1-dimethylethylsulfinamido)azetidine-1-carboxylate (1.5 g, 4.98 mmol), and ammonium acetate (1.918 g, 24.88 mmol) in MeOH (5 ml) in a 15 ml sealed tube was heated at 70° C. overnight. Analysis of the reaction mixture by LCMS showed 38% desired product with other impurities but no starting material present. The reaction mixture was used for the next step without workup.

Workup

customsealed tube

Sources & evidence

ORD record: ord-84a31348407943ba8b60694e554dd166
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096580B2

Reaction notes

Loading…