Potassium Hydroxide → HCID 54388166, compound

HRID 861445Notes

Reaction equation

HRID 861445 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C@H:13]([C:23]([O:25]CC)=[O:24])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C@H:13]([C:23]([OH:25])=[O:24])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 53744447HCID 53744447, compound

Product 1

HCID 54388166HCID 54388166, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 CH2 Cl2 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

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Sources & evidence

ORD record
ord-c1bccd7ea19d479097323e5818ee68f8
Source dataset
uspto-grants-1998_02
Patent number
US05714497

Reaction notes

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