Potassium Carbonate → HCID 86594826, compound

HRID 1373190Notes

Reaction equation

HRID 1373190 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([CH2:23][OH:24])[CH:22]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:12]=1)=[O:9])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:27].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:23]([OH:27])=[O:24])[CH:22]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:12]=1)=[O:9])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 21074210HCID 21074210, compound

Product 1

HCID 86594826HCID 86594826, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-(3-isopropoxy-5-hydroxymethyl-benzoyl) amino-5-pyridine carboxylic acid (0.33 g, 1.0 mM) in THF (20 ml) under argon, Dess-Martin periodinane (0.46 g, 1.1 mM) was added in one portion. After 45 mins satd. potassium carbonate (20 ml) was added and the THF removed in vacuo. Residue was stirred with 2.0M Na2S2O3 (3.5 ml, 7 mM) for 35 mins then acidified cautiously to pH=1 with 2M HCl. Resulting suspension was filtered, washed with water, diethyl ether, DCM and dried under high-vacuum to give 2-(3-isopropyloxy-5-carboxy-benzoyl) amino-5-pyridine carboxylic acid as a pale yellow solid (0.3 g, 93%); 1H NMR δ (d6-DMSO): 1.32 (d, 6H), 4.82 (m, 1H), 7.58 (m, 1H), 7.84 (m, 1H), 8.11 (s, 1H), 8.29 (s, 2H), 8.87 (s, 1H), 10.02 (s, 1H), 11.34 (bs, 1H).

Workup

  1. customthe THF removed in vacuo
  2. customResulting suspension
  3. filtrationwas filtered
  4. washwashed with water, diethyl ether, DCM
  5. customdried under high-vacuum

Sources & evidence

ORD record
ord-165fd215ca86496fbbf7b3425d8fa4f6
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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