Water → 3-Amino-2-(2-chlorophenyl)propyl carbamate

HRID 709125Notes

Reaction equation

HRID 709125 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH2:18][OH:19])[CH2:9][NH:10]C(=O)OC(C)(C)C.ClS([N:24]=[C:25]=[O:26])(=O)=O.O.C(=O)(O)[O-].[Na+]>C(#N)C>[C:25](=[O:26])([O:19][CH2:18][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH2:9][NH2:10])[NH2:24]

Participants

6

Reactant 4

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 66635358tert-butyl N-[2-(2-chlorophenyl)-3-hydroxypropyl]carbamate

Product 1

HCID 680324153-Amino-2-(2-chlorophenyl)propyl carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 344 mg (1.20 mmol) of the compound of Example 14A in 86 ml of acetonitrile was cooled to −15° C., and 314 μl (3.61 mmol) of chlorosulphonyl isocyanate were added. After 5 min, 10 ml of water were added and stirring of the reaction mixture was continued at 60° C. overnight. After cooling to RT, 10 ml of a saturated aqueous sodium bicarbonate solution were added. The mixture was extracted four times with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. The residue (118 mg, about 85% pure, about 37% of theory) corresponded to the title compound and was reacted further without further purification.

Workup

  1. waitwas continued at 60° C. overnight
  2. extractionThe mixture was extracted four times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. customfreed from the solvent on a rotary evaporator
  5. customwas reacted further without further purification

Sources & evidence

ORD record
ord-0e6c9778e9194e9981123a9a731ce933
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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