Triacetoxyperiodinane → n-(2-Benzooxazol-2-yl-1-methoxymethyl-2-oxo-ethyl)-2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide

HRID 1830197Notes

Reaction equation

HRID 1830197 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:43])[CH:11]([NH:15][C:16](=[O:42])[CH:17]([CH2:27][S:28]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH:39]([F:41])[F:40])(=[O:30])=[O:29])[CH2:18][C:19]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[O:20])[CH2:12][O:13][CH3:14].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+]>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[O:43])[CH:11]([NH:15][C:16](=[O:42])[CH:17]([CH2:27][S:28]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH:39]([F:41])[F:40])(=[O:30])=[O:29])[CH2:18][C:19]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[O:20])[CH2:12][O:13][CH3:14]

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22053962N-(2-benzooxazol-2-yl-2-hydroxy-1-methoxymethyl-ethyl)-2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramideHCID 22607107sodium thiosulfate NaHCO3

Product 1

HCID 10232830n-(2-Benzooxazol-2-yl-1-methoxymethyl-2-oxo-ethyl)-2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramideYield 26.1%

Procedure

This amide (150 mg, 0.24 mmol) was treated with Dess-Martin periodinane (178 mg, 0.36 mmol) at room temperature. After stirring for 1 hour, 5 ml of saturated Na2S2O3—NaHCO3 were 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 39 mg of N-(2-Benzooxazol-2-yl-1-methoxymethyl-2-oxo-ethyl)-2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide; H1 NMR(DMSO-d): 8.97, 8.8(1H, dd, J=5.6 Hz, J=5.6 Hz, NH, diastereomeric), 8.02–7.94(1H, m), 7.9–7.84(1H, m), 7.66–7.58(1H, m), 7.55–7.38(3H, m), 7.3–7.18(2H, m), 7.1(1H, t, J=73.6 Hz), 5.54–5.42(1H, m), 4.6–4.4(4H, m), 3.92–3.84(1H, m), 3.82–3.72(1H, m), 3.68–3.1(11H, m), 2.7–2.56(1H, m), 1.7–1.55(1H, m), 1.3–1(1H, m); MS: 622.4(M−1), 624.3(M+1), 646.3(M+Na).

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-6363e92771364ca586b33c8005bc81db
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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