Triacetoxyperiodinane → HCID 53241580, compound

HRID 339485Notes

Reaction equation

HRID 339485 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:24][C:25](=[O:43])[C@@H:26]([NH:34][C:35]([N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[O:36])[CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH:11]([OH:23])[C:12](=[O:22])[NH:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@H:10]([NH:24][C:25](=[O:43])[C@@H:26]([NH:34][C:35]([N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[O:36])[CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:11](=[O:23])[C:12](=[O:22])[NH:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]([CH3:18])([CH3:17])[CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67326296HCID 67326296, compound

Product 1

HCID 53241580HCID 53241580, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N4-[(1S)-2-((1S)-1-[(benzyloxy)methyl]-2-hydroxy-3-oxo-3-[(1,1,3,3-tetramethyl butyl)amino]propylamino)-1-(cyclohexylmethyl)-2-oxoethyl]-4-Morpholinecarboxamide (260 mg, 0.4 mmole) was dissolved in CH2Cl2 (4 mL). Dess-Martin periodinane (550 mg, 1.2 mmole) was added. The solution was stirred for 2 h at room temperature and quenched with Na2S2O3 and saturated bicarbonate solution. After extracting with CH2Cl2, the organic layer was dried over MgSO4, filtered, and concentrated by rotary evaporation. Purification by chromatography (silica, 1/3: Hexane/EtOAc, Rf=0.6) afforded N4-[(1S)-2-((1S)-1-[(benzyloxy)methyl]-2,3-dioxo-3-[(1,1,3,3-tetramethylbutyl)amino]propylamino)-1-(cyclohexyl-methyl)-2-oxoethyl]-4-morpholinecarboxamide as a white solid (170 mg, 71%).

Workup

  1. customquenched with Na2S2O3 and saturated bicarbonate solution
  2. extractionAfter extracting with CH2Cl2
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customPurification by chromatography (silica, 1/3: Hexane/EtOAc, Rf=0.6)

Sources & evidence

ORD record
ord-8c90e1e824f14b169f9b6dbab5237e44
Source dataset
uspto-grants-2014_11
Patent number
US08895497B2

Reaction notes

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