Sodium Hydroxide → HCID 21271738, compound

HRID 1194094Notes

Reaction equation

HRID 1194094 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([S:17](=[O:27])(=[O:26])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)=[CH:12][CH:13]=2)[CH2:8]1)C.[OH-].[Na+]>C(O)C>[Cl:25][C:21]1[CH:20]=[C:19]([NH:18][S:17]([C:11]2[CH:10]=[C:9]3[C:14]([CH2:15][CH2:16][N:7]([CH2:6][CH2:5][C:4]([OH:28])=[O:3])[CH2:8]3)=[CH:13][CH:12]=2)(=[O:26])=[O:27])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21271730HCID 21271730, compound

Product 1

HCID 21271738HCID 21271738, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl-3-[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]propionate (4.08 g) and 10% sodium hydroxide solution (10 ml) in ethanol (10 ml) was stirred at room temperature for one hour. Ethanol was removed in vacuo, water (15 ml) added and the pH was adjusted to 6-7 with 2N HCl. This was extracted with ethylacetate:methanol 4:1 (3×50 ml) and dried (MgSO4). Concentration and crystallization from ethanol-methanol gave 3-[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]propionic acid. 1.2H2O, 0.8NaCl (1.61 g, 59%); mpt. 137°-40° C.

Workup

  1. customEthanol was removed in vacuo, water (15 ml)
  2. additionadded
  3. extractionThis was extracted with ethylacetate:methanol 4:1 (3×50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration and crystallization from ethanol-methanol

Sources & evidence

ORD record
ord-30a9e9d574d743f68f2992d836c23ac7
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Reaction notes

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