Dimethyl N-cyanodithioiminocarbonate → HCID 178503934, compound

HRID 451899Notes

Reaction equation

HRID 451899 reaction equation
[NH2:1][C@@H:2]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[C:20]([N:22]=[C:23](SC)[S:24][CH3:25])#[N:21]>CC#N.CCN(CC)CC>[C:20]([N:22]=[C:23]([NH:1][C@@H:2]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])[S:24][CH3:25])#[N:21]

Participants

5

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 59201313tert-butyl (S)-2-amino-3-cyclohexylpropylmethylcarbamate

Product 1

HCID 178503934HCID 178503934, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of (S)-tert-butyl 2-amino-3-cyclohexylpropyl(methyl)carbamate (1.08 g, 4 mmol) in CH3CN (15 mL) and Et3N (3 mL) was added dimethyl cyanocarbonimidodithioate (642 mg, 4.4 mmol). The mixture was heated to reflux for 4 h. The reaction mixture was concentrated to give the residue, which was purified by column to give (S)-tert-butyl 2-((cyanoimino)(methylthio)methylamino)-3-cyclohexylpropyl(methyl)carbamate (450 mg, 31%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationThe reaction mixture was concentrated
  4. customto give the residue, which
  5. customwas purified by column

Sources & evidence

ORD record
ord-b888531826324976b4d72b4dd0a949f5
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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