Triethylamine → HCID 59464433, compound

HRID 1673254Notes

Reaction equation

HRID 1673254 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14](=[O:30])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:8][CH:7]=1)[OH:5].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14](=[O:30])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])=[CH:8][CH:7]=1)[O:5][S:40]([CH3:39])(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66911440HCID 66911440, compound

Product 1

HCID 59464433HCID 59464433, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-hydroxy-acetic acid methyl ester (9.00 g, 21.1 mmol) and triethylamine (3.20 g, 31.6 mmol) in CH2Cl2 (135 mL) cooled to −5 degrees Celsius was added dropwise methanesulfonyl chloride (3.14 g, 27.4 mmol) under N2 atmosphere. The reaction was stirred at 0 degrees Celsius until the starting material had been consumed according to TLC (about 1 hour). The mixture was washed with water (90 mL) and brine (90 mL), dried with MgSO4, filtered, and evaporated in vacuo to obtain 11.2 g (quantitative yield) of light yellow crystal which was used without further purification. MS: calc'd 505 (MH+), exp 505 (MH+).

Workup

  1. customhad been consumed
  2. customaccording to TLC (about 1 hour)
  3. washThe mixture was washed with water (90 mL) and brine (90 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-47615dad85884f79b8bd0e649610982c
Source dataset
uspto-grants-2011_08
Patent number
US07999000B2

Reaction notes

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