Triacetoxyperiodinane → HCID 86654770, compound

HRID 447166Notes

Reaction equation

HRID 447166 reaction equation
[OH:1][CH2:2][C:3]1[CH:34]=[CH:33][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([C:16](=[O:32])[C@@H:17]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:18][C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:12][CH2:11]3)[S:9][C:5]=2[CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH:2]([C:3]1[CH:34]=[CH:33][C:6]2[N:7]=[C:8]([N:10]3[CH2:11][CH2:12][N:13]([C:16](=[O:32])[C@@H:17]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:18][C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:14][CH2:15]3)[S:9][C:5]=2[CH:4]=1)=[O:1]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67237616HCID 67237616, compound

Product 1

HCID 86654770HCID 86654770, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

(S)-tert-butyl 1-(4-(6-(hydroxymethyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate (0.859 g) and Dess-Martin reagent (1.09 g) were combined in dry DCM (20 mL) and the resulting mixture stirred at room temperature for 24 hours. The resulting mixture was diluted with saturated aqueous sodium bicarbonate and then extracted with DCM. The combined organic layers were washed with saturated aqueous Na2S2O3, concentrated, and chromatographed (0 to 5% MeOH in DCM) to yield (S)-tert-butyl 1-(4-(6-formylbenzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with saturated aqueous Na2S2O3
  3. concentrationconcentrated
  4. customchromatographed (0 to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-a22a8d3774124d23b316c405e32b3e78
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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