Ammonia → 3-(1,1-Dimethylethylsulfinamido)oxetane-3-carboximidamide

HRID 1892558Notes

Reaction equation

HRID 1892558 reaction equation
[C:1]([C:3]1([NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[CH2:6][O:5][CH2:4]1)#[N:2].C([NH:17][C@H](C(O)=O)CS)(=O)C.N>CO>[CH3:11][C:10]([CH3:13])([S:8]([NH:7][C:3]1([C:1](=[NH:17])[NH2:2])[CH2:4][O:5][CH2:6]1)=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 12035N-Acetyl-L-CysteineHCID 67957830N-(3-cyanooxetan-3-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 679578843-(1,1-Dimethylethylsulfinamido)oxetane-3-carboximidamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of N-(3-cyanooxetan-3-yl)-2-methylpropane-2-sulfinamide (0.1 g, 0.494 mmol) in methanol (2 ml) in a 50 ml sealed tube was added N-acetyl-L-(+)-cysteine (0.081 g, 0.494 mmol), and the reaction mixture stirred for few minutes. A solution of ammonia in methanol (0.5 ml, 3.50 mmol, 7 N) was added, and the reaction mixture stirred at 60° C. for overnight. The reaction mixture was then concentrated under vacuum, and the crude was used for the next step without further purification.

Workup

  1. customsealed tube
  2. stirringthe reaction mixture stirred at 60° C. for overnight
  3. concentrationThe reaction mixture was then concentrated under vacuum
  4. customthe crude was used for the next step without further purification

Sources & evidence

ORD record
ord-389ccd3d7dcf458e8eba9b9d99eab6d4
Source dataset
uspto-grants-2013_08
Patent number
US08507683B2

Reaction notes

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