Methanesulfonyl chloride → HCID 22600111, compound

HRID 1760026Notes

Reaction equation

HRID 1760026 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][C:3]=1[CH2:4][OH:5].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[S:19]([O:5][CH2:4][C:3]1[CH:6]=[C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:8]=[CH:9][C:2]=1[Cl:1])(=[O:21])(=[O:20])[CH3:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54223790tert-butyl N-(4-chloro-3-(hydroxymethyl)phenyl)carbamate

Product 1

HCID 22600111HCID 22600111, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of 2-chloro-5-(Boc-amino)benzyl alcohol (7.4 g; 29 mmol; from step (i) above) in CH2Cl2 (100 mii) was added TEA (2.9 g; 29 mmol), followed by MsCl (3.3 g, 29 mmol; added dropwise). After stirring for 2 hours the resultant mixture was poured onto water. The organic layer was separated, washed with water, dried (Na2SO2) and concentrated to yield 10 g (100%) of the sub-title compound.

Workup

  1. additionadded dropwise)
  2. additionwas poured onto water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (Na2SO2)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-15ce87c16d094869a36fb95f99db0e6c
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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