2-Mesitylenesulfonyl chloride → HCID 69637295, compound

HRID 431519Notes

Reaction equation

HRID 431519 reaction equation
Cl.[C:2]([O:6][C:7](=[O:25])[C@@H:8]([NH2:24])[CH2:9][NH:10][C:11]([C:13]1[S:14][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:17]=1)=[O:12])([CH3:5])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[CH3:35][C:36]1[CH:41]=[C:40]([CH3:42])[CH:39]=[C:38]([CH3:43])[C:37]=1[S:44](Cl)(=[O:46])=[O:45]>CN(C)C=O>[C:2]([O:6][C:7](=[O:25])[C@@H:8]([NH:24][S:44]([C:37]1[C:38]([CH3:43])=[CH:39][C:40]([CH3:42])=[CH:41][C:36]=1[CH3:35])(=[O:46])=[O:45])[CH2:9][NH:10][C:11]([C:13]1[S:14][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:17]=1)=[O:12])([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69637283HCID 69637283, compound

Product 1

HCID 69637295HCID 69637295, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.490 g (1.38 mmol) of (2S)-2-amino-3-((5-(2-methoxycarbonyl-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester hydrochloride (example 15, step a) were dissolved in 15 ml of anhydrous dimethylformamide. Under stirring, 0.47 ml of N,N-diisopropyl-N-ethylamine and 0.302 g of 2,4,6-trimethylphenylsulfonyl chloride were added. Stirring was continued for 5 hours until the reaction was complete (thin layer chromatography). The solvents were removed in vacuo, and the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution and with brine. After drying with anhydrous magnesium sulfate and filtration, the solvents were removed in vacuo to give 0.623 g of a yellow oil which was sufficiently pure for use in the subsequent step.

Workup

  1. stirringStirring
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution and with brine
  5. dry with materialAfter drying with anhydrous magnesium sulfate and filtration
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-446a6c8957524fd6b72688b925f93482
Source dataset
uspto-grants-2003_12
Patent number
US06660728B2

Reaction notes

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