Triethylamine → HCID 69637309, compound

HRID 413224Notes

Reaction equation

HRID 413224 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(CC)CC)C.[F:33][C:34]([F:46])([F:45])[C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>ClCCl>[C:2]([O:6][C:7](=[O:25])[C@@H:8]([NH:24][S:41]([C:38]1[CH:37]=[CH:36][C:35]([C:34]([F:33])([F:45])[F:46])=[CH:40][CH:39]=1)(=[O:43])=[O:42])[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 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 69637283HCID 69637283, compound

Product 1

HCID 69637309HCID 69637309, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.197 g (0.5 mmol) of (2S)-2-amino-3-((5-(2-methoxycarbonyl-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester hydrochloride (example 15, step a) and triethylamine (0.14 ml, 1 mmol) in dichloromethane (5 ml) was cooled to 0° C. in an ice bath and a solution of 0.250 g (1 mmol) of 4-trifluoromethylphenylsulfonyl chloride in dichloromethane (5 ml) was added. Then the reaction mixture was stirred for 3 hours at room temperature. After removal of the solvent in vacuo the residue was absorbed onto silica gel and chromatographed with ethyl acetate/cyclohexane (1/1) to yield 0.127 g (45%) of the title compound as a white amorphous solid.

Workup

  1. customAfter removal of the solvent in vacuo the residue
  2. customwas absorbed onto silica gel
  3. customchromatographed with ethyl acetate/cyclohexane (1/1)

Sources & evidence

ORD record
ord-07818a7debfb4db7954497a45145269c
Source dataset
uspto-grants-2003_05
Patent number
US06566366B1

Reaction notes

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