Triethylamine → HCID 69637268, compound

HRID 431521Notes

Reaction equation

HRID 431521 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.[C:33]([C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1)([CH3:36])([CH3:35])[CH3:34]>ClCCl>[C:2]([O:6][C:7](=[O:25])[C@@H:8]([NH:24][S:43]([C:40]1[CH:41]=[CH:42][C:37]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:38][CH:39]=1)(=[O:45])=[O:44])[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 1398824-t-Butylbenzenesulfonyl chlorideHCID 69637283HCID 69637283, compound

Product 1

HCID 69637268HCID 69637268, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.395 g (1 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 (0.15 ml, 1.1 mmol) in dichloromethane (10 ml) was cooled to 0° C. in an ice bath and a solution of 0.255 g (1.1 mmol) of 4-tert-butylphenylsulfonyl chloride in dichloromethane (5 ml) was added. Then the reaction mixture was stirred at room temperature overnight. After removal of the solvent in vacuo the residue was absorbed onto silica gel and chromatographed with ethyl acetate/cyclohexane (1/1) to yield 0.285 g (52%) 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-801bb0b0f5654cd7b6d5d955b23d218f
Source dataset
uspto-grants-2003_12
Patent number
US06660728B2

Reaction notes

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