Triacetoxyperiodinane → HCID 68713725, compound

HRID 1818816Notes

Reaction equation

HRID 1818816 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:27])[CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:11]1(=[O:26])=[O:25])([CH3:4])([CH3:3])[CH3:2].[C:28]([O:32][C:33](=[O:35])[NH2:34])([CH3:31])([CH3:30])[CH3:29].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([NH:5][CH2:6][C:7](=[O:27])[CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[S:11]1(=[O:26])=[O:25])([CH3:4])([CH3:2])[CH3:3].[C:28]([O:32][C:33](=[O:35])[NH2:34])([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68712066HCID 68712066, compound

Product 1

HCID 68713725HCID 68713725, compoundYield 147%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(tert-butylamino)-4-(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)butan-2-ol-carbamic acid tert-butyl ester (15 mg, 0.031 mmol) and Dess Martin periodinane (20 mg, 0.046 mmol) were stirred in dichloromethane (5 mL) in a sealed vial at room temperature for 18 hr. The reaction mixture was concentrated then loaded directly onto silica gel and purified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane to afford 0.023 g of 1-(tert-butylamino)-4-(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)butan-2-one-carbamic acid tert-butyl ester as a clear oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6020ec7074174bc8bb6508eef28775b2
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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