Pyridine → N-[(1R)-2-[(Methylsulfonyl)oxy]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester

HRID 256004Notes

Reaction equation

HRID 256004 reaction equation
N1C=CC=CC=1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].[C:12]([O:16][C:17]([NH:19][C@H:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:21][OH:22])=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[C:12]([O:16][C:17]([NH:19][C@H:20]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:21][O:22][S:8]([CH3:7])(=[O:10])=[O:9])=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 7016461Carbamic acid, N-((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl ester

Product 1

HCID 11723227N-[(1R)-2-[(Methylsulfonyl)oxy]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11 ml of pyridine and then 6.6 ml of methanesulfonyl chloride were added dropwise, at room temperature, to a solution containing 9.9 g of 2(R)-t-butoxycarbonylamino-2-phenylethanol [prepared as described in step (a) above] dissolved in 120 ml of methylene chloride. This mixture was stirred for 15 hours at room temperature, after which the solvent was removed by distillation. The residue was dissolved in ethyl acetate and water and the ethyl acetate layer was separated. This layer was washed with an aqueous solution of potassium hydrogen sulfate and an aqueous solution of sodium bicarbonate and then dried over anhydrous magnesium sulfate, after which the solvent was distilled off. The crystalline residue was collected by filtration and washed with a small amount of diisopropyl ether and cyclohexane to give 12.2 g of the title compound, melting at 108°-109° C.

Workup

  1. customafter which the solvent was removed by distillation
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. customwater and the ethyl acetate layer was separated
  4. washThis layer was washed with an aqueous solution of potassium hydrogen sulfate
  5. dry with materialan aqueous solution of sodium bicarbonate and then dried over anhydrous magnesium sulfate
  6. distillationafter which the solvent was distilled off
  7. filtrationThe crystalline residue was collected by filtration
  8. washwashed with a small amount of diisopropyl ether and cyclohexane

Sources & evidence

ORD record
ord-e3db372fca0d460bb39884e7a1ac3816
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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