Pyridine → Carbamic acid, (2-chloro-2-phenylethyl)-, 1,1-dimethylethyl ester

HRID 256010Notes

Reaction equation

HRID 256010 reaction equation
N1C=CC=CC=1.CS([Cl:11])(=O)=O.[C:12]([O:16][C:17]([NH:19][CH2:20][CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)O)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[C:12]([O:16][C:17]([NH:19][CH2:20][CH:21]([Cl:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 9816137tert-butyl N-(2-hydroxy-2-phenylethyl)carbamate

Product 1

HCID 20164905Carbamic acid, (2-chloro-2-phenylethyl)-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.7 ml of pyridine and 2.2 ml of methanesulfonyl chloride was added dropwise to 35 ml of a solution of 3.5 g of 2-t-butoxycarbonylamino-1-phenylethanol [prepared as described in step (a) above] in methylene chloride and the reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was condensed by evaporation under reduced pressure, and the residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated, washed with water and then washed with an aqueous solution of potassium hydrogen sulfate and with an aqueous solution of sodium bicarbonate. The resulting solution was dried over anhydrous magnesium sulfate. The solvent was then distilled off. The residue was subjected to silica gel column chromatography using a 15:85 by volume mixture of ethyl acetate and cyclohexane as the eluent, to give 0.75 g of the title compound as crystals melting at 57°-59° C.

Workup

  1. customcondensed
  2. customby evaporation under reduced pressure
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed with water
  6. washwashed with an aqueous solution of potassium hydrogen sulfate and with an aqueous solution of sodium bicarbonate
  7. dry with materialThe resulting solution was dried over anhydrous magnesium sulfate
  8. distillationThe solvent was then distilled off
  9. additionby volume mixture of ethyl acetate and cyclohexane as the eluent

Sources & evidence

ORD record
ord-9d104671dae6416aa1b3d071dae842f6
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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