Triacetoxyperiodinane → HCID 69436793, compound

HRID 1830176Notes

Reaction equation

HRID 1830176 reaction equation
[OH:1][CH:2]([C:30]1[O:31][C:32]([CH2:35][O:36][CH3:37])=[N:33][N:34]=1)[CH:3]([NH:6][C:7](=[O:29])[C:8]([CH3:28])([S:18]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:20])=[O:19])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11])[CH2:4][CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>>[CH3:37][O:36][CH2:35][C:32]1[O:31][C:30]([C:2]([CH:3]([NH:6][C:7](=[O:29])[C:8]([CH3:28])([S:18]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:20])=[O:19])[CH2:9][C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[O:11])[CH2:4][CH3:5])=[O:1])=[N:34][N:33]=1

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22053947HCID 22053947, compoundHCID 22607107sodium thiosulfate NaHCO3

Product 1

HCID 69436793HCID 69436793, compound

Procedure

This amide then was treated with Dess-Martin periodinane (111 mg, 0.149 mmol) at room temperature. After stirring for 1 hour, 5 mls of saturated Na2S2O3—NaHCO3 was added. After a further 0.5 hours, the reaction mixture was extracted with ethyl acetate, washed with brine, dried with MgSO4 and concentrated. The residue was purified with silica gel column chromatography to yield 13 mgs of N-[1-(5-Methoxymethyl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-morpholin-4-yl-4-oxo-2-benzylsulfonyl-methyl-butyramide; H1 NMR(CDCl3): 7.8, 7.5(1H, d,d NH, diastereomeric), 7.4–7.2(5H, m), 5.3–5.1(1H, m), 4.6(2H, s, OCH2), 4.3–4.1(3H, m), 3.8–3.1(13H, m), 3–2.4(2H, m), 2.2–1.5(2H, m), 0.95(3H, t); MS: 535.7(M−1), 537.5(M+1).

Workup

  1. waitAfter a further 0.5 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-54c227f14c1a4b5dbad450895836ef00
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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