Triacetoxyperiodinane → HCID 89253130, compound

HRID 923545Notes

Reaction equation

HRID 923545 reaction equation
[CH2:1]([O:8][C:9]1[CH:40]=[CH:39][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:34][CH2:35][CH2:36][CH2:37][OH:38])[C:24](=[O:33])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CC(=O)OCC>[CH2:1]([O:8][C:9]1[CH:40]=[CH:39][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:34][CH2:35][CH2:36][CH:37]=[O:38])[C:24](=[O:33])[C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 89253163HCID 89253163, compound2×

Product 1

HCID 89253130HCID 89253130, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared from compound 87: To a stirring solution of 4-((N-(4-hydroxybutyl)-4-methoxybenzamido)methyl)phenyl 4-(heptyloxy)benzoate 87 (258 mg, 0.484 mmol) in DCM was added sodium bicarbonate (81 mg, 0.968 mmol) and Dess-Martin periodinane (308 mg, 0.726 mmol). The reaction mixture was stirred at room temperature for 2 h. The crude reaction was diluted with EA followed by NaHCO3 and aq. NaS2O3. The biphasic mixture was stirred overnight at room temperature. The organic phase was separated, washed with NaHCO3, dried over MgSO4, and concentrated to yield 264 mg of crude 4-((4-methoxy-N-(4-oxobutyl)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-8. LCMS-ESI (m/z) calculated for C33H39NO6: 545; found 546 [M+H]+, tR=3.14 min (Method 3).

Workup

  1. customThe crude reaction
  2. stirringThe biphasic mixture was stirred overnight at room temperature
  3. customThe organic phase was separated
  4. washwashed with NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d727a3dd019d4614a3fee8c4eeeb410b
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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