Water → HCID 57345279, compound

HRID 1847125Notes

Reaction equation

HRID 1847125 reaction equation
O.[OH-].[Na+:3].[NH2:4][CH2:5][CH2:6][S:7]([OH:10])(=[O:9])=[O:8].[C:11](Cl)([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>C1(C)C=CC=CC=1>[Na+:3].[C:11]([NH:4][CH2:5][CH2:6][S:7]([O-:10])(=[O:9])=[O:8])([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1123TaurineHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 57345279HCID 57345279, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 1000 ml of water in the RBF charge 192 gm of (3.0 eq) of sodium hydroxide under cooling followed by 200 gm of Taurine and dissolve it until clear solution is obtained. Cool to 0° C. to 5° C., and Charge 50% CBZ-Cl in toluene at 0° C. to 5° C. After completion of addition, maintain at room temperature for 14 h. Separate the toluene layer and wash the aqueous layer with 2×200 ml of ethyl acetate. Add slowly 27 gm of sodium hydroxide in 60 ml of water to the aqueous layer and adjust pH to 12-14. Cool to 0° C. to 5° C. and a white solid separates from the solution. Filter the solid and dry the solid at 60-70° C. Weight of the solid: 320 g

Workup

  1. temperatureunder cooling
  2. dissolutiondissolve it until clear solution
  3. customis obtained
  4. temperatureCool to 0° C. to 5° C.
  5. additionAfter completion of addition
  6. customSeparate the toluene layer
  7. washwash the aqueous layer with 2×200 ml of ethyl acetate
  8. additionAdd slowly 27 gm of sodium hydroxide in 60 ml of water to the aqueous layer
  9. temperatureCool to 0° C. to 5° C.
  10. filtrationFilter the solid
  11. customdry the solid at 60-70° C

Sources & evidence

ORD record
ord-6b69c5d9171648709f2dce241b4a375c
Source dataset
uspto-grants-2015_02
Patent number
US08952148B2

Reaction notes

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