Potassium Carbonate → 2-{[Methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-4-(pyridin-2-yloxy)-benzoic acid ethyl ester

HRID 1480977Notes

Reaction equation

HRID 1480977 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:6]=1[CH2:18]Br)[CH3:2].[NH:21]([S:27]([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH2:22][C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:6]=1[CH2:18][N:21]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[S:27]([C:30]1[CH:31]=[CH:32][C:33]([CH3:34])=[CH:35][CH:36]=1)(=[O:29])=[O:28])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 562880Methyl 2-(4-methylphenylsulfonamido)acetateHCID 898128232-Bromomethyl-4-(pyridin-2-yloxy)-benzoic acid ethyl ester

Product 1

HCID 898129952-{[Methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-4-(pyridin-2-yloxy)-benzoic acid ethyl esterYield 72.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-bromomethyl-4-(pyridin-2-yloxy)-benzoic acid ethyl ester (855 mg, crude from previous step), Ts-Gly-OMe (502 mg), potassium carbonate (425 mg) and KI (32 mg) in DMF (10 mL) was stirred at rt overnight. Then the reaction mixture was diluted with EtOAc, washed with water, diluted NaCl sol and dried over anhydrous sodium sulfate, filtered, concentrated and the residue was column purified to give product (745 mg). LC MS ESI+: 499 (M+1)+.

Workup

  1. washwashed with water, diluted NaCl sol
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-6017f8adb8414c2fb098db73c02b12c3
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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