Methanesulfonyl chloride → HCID 13857264, compound

HRID 1757303Notes

Reaction equation

HRID 1757303 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:17][OH:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([O:18][CH2:17][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 7019371N-Boc-D-phenylalaninol

Product 1

HCID 13857264HCID 13857264, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butoxycarbonyl-D-Phenylalaninol (754 mg) and TEA (0.5 ml) in dichloromethane was added methanesulfonyl chloride (0.28 ml) at 0°~5 ° C. The reaction mixture was stirred at 0°~5 ° C. for 30 min, quenched with water, and extracted with dichloromethane. The organic layer was washed with 10% citric acid and sat. NaHCO, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/hexane=1/2 to afford the product (931 mg).

Workup

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with 10% citric acid and sat. NaHCO
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate/hexane=1/2

Sources & evidence

ORD record
ord-2d1093498fbf46b4a0c1eae13bfacfbd
Source dataset
uspto-grants-1995_08
Patent number
US05444152

Reaction notes

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