Triacetoxyperiodinane → HCID 72408143, compound

HRID 722748Notes

Reaction equation

HRID 722748 reaction equation
[OH:1][CH2:2][CH:3]([NH:12][C:13]([CH:15]1[N:20]2[C:21](=[O:40])[CH:22]([NH:27][C:28]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)=[O:29])[CH2:23][CH:24]=[CH:25][CH2:26][CH:19]2[CH2:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]([NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:1][CH:2]1[CH:3]([NH:12][C:13]([CH:15]2[N:20]3[C:21](=[O:40])[CH:22]([NH:27][C:28]([C:30]4[CH:39]=[CH:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH:31]=4)=[O:29])[CH2:23][CH:24]=[CH:25][CH2:26][CH:19]3[CH2:18][CH2:17][CH2:16]2)=[O:14])[CH2:4][C:5](=[O:6])[N:7]1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86590810HCID 86590810, compound

Product 1

HCID 72408143HCID 72408143, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[(Naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid (1-hydroxymethyl-3-methanesulfonylamino-3-oxo-propyl)-amide, 117, (49 mg) is dissolved in 5 mL methylene chloride and cooled to 0 deg. Dess-Martin periodinane (90 mg) is added, and the reaction is strirred for 2 h at 0 deg. Saturated aqueous sodium bicarbonate solution is added and the mixture is extracted with ethyl acetate. The combined opganic layers are dried over sodium sulfate powder and the product is purified over silica (2% methanol in methylene chloride) to afford the desired product.

Workup

  1. temperaturecooled to 0 deg
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe combined opganic layers are dried over sodium sulfate powder
  4. customthe product is purified over silica (2% methanol in methylene chloride)

Sources & evidence

ORD record
ord-eb018ca63b8d4ee9bcf936101a5c6cea
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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