Hydrochloric Acid → N-[4-(hexadecylamino)benzoyl]-2-aminoethanesulfonic acid

HRID 1980190

Reaction equation

HRID 1980190 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5].FC(F)(F)C([N:12]([C:29]1[CH:44]=[CH:43][C:32]([C:33](ON2C(=O)CCC2=O)=[O:34])=[CH:31][CH:30]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=O.[OH-].[Na+].Cl>O.C(O)C.C(N(CC)CC)C>[CH2:13]([NH:12][C:29]1[CH:30]=[CH:31][C:32]([C:33]([NH:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5])=[O:34])=[CH:43][CH:44]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1123TaurineHCID 14798Sodium HydroxideHCID 20437360N-[N-trifluoroacetyl-4-(hexadecylamino)benzoyloxy]succinimide

Product 1

HCID 20437369N-[4-(hexadecylamino)benzoyl]-2-aminoethanesulfonic 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-[p-(2,2,2-trifluoro-N-hexadecylacetamido)benzoyloxy]succinimide as a solution in 45 ml. of ethanol. After 24 hours, the mixture is treated with 20 ml. of 2.0M sodium hydroxide and 25 ml. of water. After stirring for 10 min., 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, m.p. 190°-220° C.

Workup

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

Sources & evidence

ORD record
ord-4f1078d0a78644cfa4c9be30d442e760
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Linked notes

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