4-Toluenesulfonyl chloride → Tosyl valine, D-

HRID 395917Notes

Reaction equation

HRID 395917 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH2:12][C@@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15]>C(OCC)C.[OH-].[Na+]>[S:1]([NH:12][C@@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 71563D-Valine

Product 1

HCID 708671Tosyl valine, D-

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of tosyl chloride (20 g, 0.1 mol) in diethyl ether (100 ml) was added in drops at room temperature to a solution of D-valine (11.7 g, 0.1 mol) in 200 ml of 1N NaOH, and the two-phase mixture was stirred vigorously for 4 hours. Then, the diethyl ether phase was separated, the aqueous phase was washed twice more with diethyl ether and acidified at 0° C. by adding concentrated HCl. After 30 minutes, it was suctioned off, liberally rewashed with ice water and dried for several hours at 0.01 Torr. 18.1 g, (67%), of colorless crystals was obtained (melting point: 147° C.).

Workup

  1. customThen, the diethyl ether phase was separated
  2. washthe aqueous phase was washed twice more with diethyl ether
  3. customacidified at 0° C.
  4. additionby adding concentrated HCl
  5. waitAfter 30 minutes
  6. customdried for several hours at 0.01 Torr
  7. custom18.1 g, (67%), of colorless crystals was obtained (melting point: 147° C.)

Sources & evidence

ORD record
ord-e24132774b42475ba8cdcfb15309f12d
Source dataset
uspto-grants-2003_08
Patent number
US06605726B1

Reaction notes

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