Hydrochloric Acid → N-[2-(4-tetradecenylamino)benzoyl]-2-amino ethanesulfonic acid

HRID 325568

Reaction equation

HRID 325568 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5].FC(F)(F)C([N:12]([C:27]1[CH:42]=[CH:41][CH:40]=[CH:39][C:28]=1[C:29](ON1C(=O)CCC1=O)=[O:30])[CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=O.[OH-].[Na+].Cl>O.C(O)C.C(N(CC)CC)C>[CH2:13]([NH:12][C:27]1[CH:42]=[CH:41][CH:40]=[CH:39][C:28]=1[C:29]([NH:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5])=[O:30])[CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1123TaurineHCID 14798Sodium HydroxideHCID 73708092N-{2-[2,2,2-trifluoro-N-(4-tetradecenyl)acetamido]benzoyloxy}succinimide

Product 1

HCID 54450014N-[2-(4-tetradecenylamino)benzoyl]-2-amino ethanesulfonic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 2.50 g. of taurine and 5.6 ml. of triethylamine in 22.5 ml. of water is added 5.55 g. of N-{2-[2,2,2-trifluoro-N-(4-tetradecenyl)acetamido]benzoyloxy}succinimide as a solution in 45 ml. of ethanol. After 24 hours, the mixture is treated with 20 ml. of 2.0 M sodium hydroxide and 25 ml. of water. After stirring for 10 minutes, the mixture is acidified with dilute hydrochloric acid, and the crude product is collected by filtration. Recrystallization affords the title compound as a white solid.

Workup

  1. additionthe mixture is treated with 20 ml
  2. filtrationthe crude product is collected by filtration
  3. customRecrystallization

Sources & evidence

ORD record
ord-70b34643be644e698e99a0a0c8f2952b
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Linked notes

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