Triacetoxyperiodinane → HCID 11504537, compound

HRID 601530Notes

Reaction equation

HRID 601530 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]([C:20]2[S:24][C:23]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[N:22][C:21]=2[CH2:32][CH2:33]O)=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.[OH-].[Na+]>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]2[S:24][C:20]3[C:18](=[O:19])[N:17]([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][N:12]5[CH2:13][CH2:14][CH2:15][CH2:16]5)=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:33]=[CH:32][C:21]=3[N:22]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57501766HCID 57501766, compound

Product 1

HCID 11504537HCID 11504537, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Mix 2-(4-chloro-phenyl)-4-(2-hydroxy-ethyl)-thiazole-5-carboxylic acid [3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide (80 mg, 0.16 mmol) and Dess-Martin periodinane (70 mg, 0.1 6 mmol) in CH2Cl2 and stir at RT for 48 h. Dilute the mixture with aqueous 1 N NaOH and extract with CH2Cl2. Dry, filter, and concentrate the organic solution. Purify the crude material by flash chromatography, using a gradient of 100% EtOAc to 12% 2 N NH3/MeOH in EtOAc, to give the title compound (12 mg, 16%). MS (ES+) 482.0 (M+1)+. 1H NMR (400 MHz, DMSO-d6): δ 8.01 (d, 2H, J=8.8 Hz), 7.46 (d, 2H, J=8.3 Hz), 7.40 (d, 1H, J=7.0 Hz), 7.34 (s, 1H), 6.89-6.99 (m, 3H), 4.20 (t, 2H, J=6.4 Hz), 3.86 (s, 3H), 2.96 (t, 2H, J=6.4 Hz), 2.64 (s, 4H), 1.80 (m, 4H).

Workup

  1. extractionextract with CH2Cl2
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate the organic solution
  5. customPurify the crude material by flash chromatography

Sources & evidence

ORD record
ord-e6c0a383c1e04a82819d5a7ea1a566d3
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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