Water → HCID 22000405, compound

HRID 917499Notes

Reaction equation

HRID 917499 reaction equation
Cl.[NH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5]1.C(N(C(C)C)CC)(C)C.[C:30]([N:38]=[C:39]=[S:40])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>C1COCC1>[CH2:13]([O:12][C:11](=[O:20])[NH:10][CH:7]1[CH2:8][CH2:9][CH:4]([CH2:3][NH:2][C:39]([NH:38][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[S:40])[CH2:5][CH2:6]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 68284Benzoyl isothiocyanateHCID 81531DiisopropylethylamineHCID 22990186trans-4-(Cbz-amino)cyclohexanemethanamine hydrochloride

Product 1

HCID 22000405HCID 22000405, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl N-[4-(aminomethyl)cyclohexyl]carbamate HCl (3.46 g, 11.6 mmol) and diisopropylethylamine (6.0 ml) in anhydrous THF (90 ml) was stirred at room temperature for 20 minutes. To this solution was added benzoylisothiocyanate (2.00 g, 12.3 mmol) and the reaction mixture stirred at room temperature for 14 hours. The solution was poured into water (200 ml) and extracted with Et2O (2×150 ml). The organic layer was dried over MgSO4, filtered and evaporated to yield a solid. The solid was triturated with hexane and filtered to yield 99% (5.023 g) of the desired product.

Workup

  1. extractionextracted with Et2O (2×150 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a solid
  6. customThe solid was triturated with hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-48471f07f77b46d588df4a66eda5d75a
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

Loading…