Cyanamidnatrium → 1-cyano-3-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)thiourea

HRID 1254380Notes

Reaction equation

HRID 1254380 reaction equation
[CH:1]1([CH2:7][C@H:8]([N:21]=[C:22]=[S:23])[CH2:9][N:10]([CH3:20])[C:11](=[O:19])[O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:24]#[C:25][NH2:26].[Na]>C(O)C.[NH4+].[Cl-].O>[C:25]([NH:26][C:22]([NH:21][C@@H:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH2:9][N:10]([CH3:20])[C:11]([O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])=[O:19])=[S:23])#[N:24]

Participants

5

Reactant 2

HCID 57375518CyanamidnatriumHCID 86653085(2-(trimethylsilyl)ethyl) (S)-3-cyclohexyl-2-isothiocyanatopropyl-methylcarbamate

Product 1

HCID 866530841-cyano-3-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)thioureaYield 108.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57429219Ammonium chloride monohydrateSolvent

Procedure

To a stirred solution of (2-(trimethylsilyl)ethyl) (S)-3-cyclohexyl-2-isothiocyanatopropyl-methylcarbamate (190 mg, 0.53 mmol) in ethanol (5 mL) was added solid sodium hydrogen cyanamide (38 mg, 0.59 mmol). The mixture was stirred at rt for 2 d, diluted with 1:1 sat'd aq NH4Cl/H2O (40 mL) and extracted with ether (2×60 mL). The combined ether extracts were dried over MgSO4 and rotovaped to leave 1-cyano-3-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)thiourea (230 mg, quant) as a white solid.

Workup

  1. extractionextracted with ether (2×60 mL)
  2. dry with materialThe combined ether extracts were dried over MgSO4

Sources & evidence

ORD record
ord-a489085ec2124902ab404441cb1b08ef
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

Loading…