Triethylamine → HCID 59164492, compound

HRID 1894094Notes

Reaction equation

HRID 1894094 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14].CCN(CC)CC.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59164513HCID 59164513, compound

Product 1

HCID 59164492HCID 59164492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-acetylamino-4-hydroxymethyl-benzoic acid methyl ester (4 g, 17.9 mmol) and Et3N (7.5 mL, 3.0 equiv) in DCM (100 mL) at 0° C. was added MsCl (2.1 mL, 1.5 equiv) dropwise. At the end of the addition, the mixture was stirred 1 h at 0° C. The organic phase was washed with a saturated solution of NaHCO3 and then dried (Na2SO4). The solution was concentrated in vacuo to afford the title compound as a brown paste (5.4 g, 100%) (ES-MS: m/z 302.2 [M+H]+, rt 4.58 min).

Workup

  1. additionAt the end of the addition
  2. washThe organic phase was washed with a saturated solution of NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-3104ca879c5b4da9b40503900a5072b1
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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