Sodium periodate → HCID 89590877, compound

HRID 522418Notes

Reaction equation

HRID 522418 reaction equation
[C:1]([C@H:5]1[C:33](=[O:34])[N:32]2[CH2:35][C@@H:29]([CH2:30][C@H:31]2[C:36]([O:38][CH3:39])=[O:37])[O:28][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([CH:26]=C)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:40][C@H:9]2[O:8][C:7](=[O:41])[NH:6]1)([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:43].[Na+]>CC(C)=O.O>[C:1]([C@H:5]1[C:33](=[O:34])[N:32]2[CH2:35][C@@H:29]([CH2:30][C@H:31]2[C:36]([O:38][CH3:39])=[O:37])[O:28][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([CH:26]=[O:43])=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:40][C@H:9]2[O:8][C:7](=[O:41])[NH:6]1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 23667635Sodium periodate2×HCID 89590961HCID 89590961, compound

Product 1

HCID 89590877HCID 89590877, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of the product from Step 1 (30 mg, 0.053 mmol) in acetone (1 ml) and water (1 mL) was added potassium osmate dehydrate (19.61 mg, 0.053 mmol). The reaction was stirred at room temperature for 10 minutes after which sodium periodate (114 mg, 0.532 mmol) was added. After stirring for 2 hours, an additional 15 mg of potassium osmate and 115 mg of sodium periodate were added. After stirring 16 hours, the reaction was filtered and the solid was washed with acetone. The filtrate was concentrated, diluted with EtOAc and washed with Na2S2O3 and NaHCO3 aq. soln. Purification by PTLC (30% EtOAc-hexane) provided the desired aldehyde.

Workup

  1. additionwas added
  2. stirringAfter stirring 16 hours
  3. filtrationthe reaction was filtered
  4. washthe solid was washed with acetone
  5. concentrationThe filtrate was concentrated
  6. additiondiluted with EtOAc
  7. washwashed with Na2S2O3 and NaHCO3 aq. soln
  8. customPurification by PTLC (30% EtOAc-hexane)

Sources & evidence

ORD record
ord-ce37f047a3d64c04b015fd110491f10a
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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