Benzenesulfonyl chloride, 3,4-dichloro- → HCID 53744447, compound

HRID 1720451Notes

Reaction equation

HRID 1720451 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][C@@H:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH2:21])=[CH:17][CH:16]=1>C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:21][C@H:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:28][CH:27]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 53853012HCID 53853012, compound

Product 1

HCID 53744447HCID 53744447, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

5 g of 3,4-dichlorophenylsulphonyl chloride are introduced, with stirring, into a mixture of 3,8 g of ethyl O-methyltyrosinate in 35 ml of CH2Cl2 and 50 ml of a saturated aqueous potassium carbonate solution. After one night, the solid is removed, the organic phase separated and the aqueous phase reextracted with CH2Cl2. The dried organic phases are concentrated and the residue is chromatographed on a silica column, eluting with a mixture of CH2Cl2 and CH3OH (95/5-V/V). 6.8 g of racemic ethyl N-(3,4-dichlorophenylsulphonyl)-O-methyltyrosinate are obtained, which product melts at 99° C. This ester is hydrolysed in 100 ml of C2H5OH containing 9.5 ml of a 5N aqueous KOH solution to give, after acidification, 5.5 g of the corresponding acid which melts at 183° C.

Workup

  1. waitAfter one night
  2. customthe solid is removed
  3. customthe organic phase separated
  4. concentrationThe dried organic phases are concentrated
  5. customthe residue is chromatographed on a silica column
  6. washeluting with a mixture of CH2Cl2 and CH3OH (95/5-V/V)

Sources & evidence

ORD record
ord-afe47917dd244ac59c540f6388efc266
Source dataset
uspto-grants-1996_04
Patent number
US05506258

Reaction notes

Loading…