Taurine → HCID 23668071, compound

HRID 565824Notes

Reaction equation

HRID 565824 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.NCCS(O)(=O)=O.C1COCC1.[OH-].[Na+:42]>C1C=CC=CC=1.CN(C=O)C>[Na+:42].[C:11]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([O-:10])=[O:9])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 1123TaurineHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 68992Triphenylacetic acid

Product 1

HCID 23668071HCID 23668071, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

Triphenylacetic acid (2 g, 6.94 mmol) was dissolved in 5 mL of benzene in a round bottom flask. One drop of DMF was added as a catalyst and the solution was cooled with an ice bath. Once the solution had cooled oxalyl chloride (3 mL, 34.7 mmol) was added dropwise resulting in a vigorously bubbling solution. The reaction was allowed to stir 3 hours and the volatiles were removed under vacuum. The resulting oil was dissolved in 25 mL of THF and the round bottom flask was fitted with an addition funnel. The solution was cooled and a solution of taurine (1.3 g, 11.6 mmol) in 13 mL of 1 N NaOH was mixed with 12 mL of THF and the solution was placed into the addition funnel and added dropwise. The reaction was stirred overnight and the THF was removed by rotary evaporation. The resulting solid was collected and washed with water. The material was then recrystallized from water providing 2.5 g (90%) of light yellow plates. IR (KBr): 3439 (N—H), 2763 (br), 1655 (C═O), 1218. 1H NMR (CDCl3/DMSO-d6, 300 MHz): δ 2.58 (t, J=22, 1H); 2.75 (t, J=22 Hz, 6H); 2.92 (dt, J=18, 22, 1H); 3.48 (s, 6H); 3.562 (dt, J=22,18 Hz, 1H); 7.17-7.30 (m, 16H); 7.42 (t, J=18 Hz, 0.5H)); 13C NMR (CDCl3/DMSO-d6, 75.4 MHz): δ 172.0 (C), 143.5 (C),130.2 (CH), 127.5 (CH), 126.4 (CH), 67.3 (C), 52 (CH2), 49.8 (CH2), 37.67 (CH2), 36.3 (CH2).

Workup

  1. temperaturethe solution was cooled with an ice bath
  2. additionwas added dropwise
  3. customresulting in a vigorously bubbling solution
  4. customthe volatiles were removed under vacuum
  5. dissolutionThe resulting oil was dissolved in 25 mL of THF
  6. customthe round bottom flask was fitted with an addition funnel
  7. temperatureThe solution was cooled
  8. additionadded dropwise
  9. stirringThe reaction was stirred overnight
  10. customthe THF was removed by rotary evaporation
  11. customThe resulting solid was collected
  12. washwashed with water
  13. customThe material was then recrystallized from water providing 2.5 g (90%) of light yellow plates

Sources & evidence

ORD record
ord-3ed57e9d60d4411e9f93169a3b984bb9
Source dataset
uspto-grants-2001_01
Patent number
US06172262B2

Reaction notes

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