4-Toluenesulfonyl chloride → Trp(Tos)-OBzl

HRID 1649339

Reaction equation

HRID 1649339 reaction equation
[NH2:1][C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[H-].[Na+].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(OCC)(=O)C>CN(C)C=O.O>[NH2:1][C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[CH:5]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 7016092L-Tryptophan benzyl ester

Product 1

HCID 131713224Trp(Tos)-OBzl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (DMF) (10 ml) was dissolved Tr-Trp-OBzl (2.15 g, 4 mM), followed by addition of sodium hydride (50% in mineral oil, the same applies below; 240 mg, 5 mM) in a nitrogen gas stream. The reaction was conducted at room temperature for 20 minutes, after which p-toluenesulfonyl chloride (950 mg, 5 mM) was added. The reaction was further carried out at room temperature for 15 hours, at the end of which time ethyl acetate (50 ml) was added and the mixture was stirred for one hour. To the reaction mixture was added water (30 ml) with caution and the organic layer was taken and washed with 5% aqueous sodium hydrogen carbonate and water. After drying over sodium sulfate, the ethyl acetate was distilled off. The residue was purified by column chromatography on silica gel (15 g) using toluene as the solvent to give Tr-Trp(Tos)-OBzl. Yield 1.70 g (61.5%); m.p. 101°-103° C.; [α]D24 +47.6° (c=0.5, DMF).

Workup

  1. additionwas added
  2. washwashed with 5% aqueous sodium hydrogen carbonate and water
  3. dry with materialAfter drying over sodium sulfate
  4. distillationthe ethyl acetate was distilled off
  5. customThe residue was purified by column chromatography on silica gel (15 g)

Sources & evidence

ORD record
ord-238004af3a314d198c685971ec4c51f1
Source dataset
uspto-grants-1983_11
Patent number
US04416820

Linked notes

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