Sodium Hydroxide → HCID 18612898, compound

HRID 1420605Notes

Reaction equation

HRID 1420605 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:6][C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO.O1CCCC1>[NH2:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18612921HCID 18612921, compound

Product 1

HCID 18612898HCID 18612898, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5.14 g (14.1 mmol) of methyl 2-[(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]acetate in 50 ml of methanol-tetrahydrofuran (1:1) was added 2.86 ml of 10 N NaOH and the mixture refluxed for 2 hours. The solvent was removed under vacuum and the residue partitioned between water and ether. The water layer was separated and acidified with 2 N citric acid. The solid was filtered, washed with H2O and dried in a vacuum oven at room temperature to give 4.45 g (91%) of crystals, m.p. 145°-147° C. Anal. for C16H18N2O5S: Calc'd: C,54.9; H,5.2; N,8.0; Found: C,55.1; H,5.2; N,7.9.

Workup

  1. temperaturethe mixture refluxed for 2 hours
  2. customThe solvent was removed under vacuum
  3. customthe residue partitioned between water and ether
  4. customThe water layer was separated
  5. filtrationThe solid was filtered
  6. washwashed with H2O
  7. customdried in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-2530bb922abd40c9994cea961bb1a1d1
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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