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

HRID 2355498Notes

Reaction equation

HRID 2355498 reaction equation
[CH3:1][Si:2]([CH3:23])([CH3:22])[CH2:3][CH2:4][O:5][C:6](=[O:21])[N:7]([CH2:9][C@@H:10]([N:18]=[C:19]=[S:20])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH3:8].[N:24]#[C:25][NH2:26].[Na]>C(O)C.[NH4+].[Cl-].O>[C:25]([NH:26][C:19]([NH:18][C@@H:10]([CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[CH2:9][N:7]([CH3:8])[C:6]([O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:22])[CH3:23])=[O:21])=[S:20])#[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-90784330934c4cedb8da7893289ad480
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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