3-{[1,1-dioxido-2-(phenylmethyl)-3,4-dihydro-2H-5,1,2-benzoxathiazepin-7-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide → 3-[(1,1-Dioxido-3,4-dihydro-2H-5,1,2-benzoxathiazepin-7-yl)oxy]-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 548676Notes

Reaction equation

HRID 548676 reaction equation
[O:1]=[S:2]1(=[O:41])[C:8]2[CH:9]=[CH:10][C:11]([O:13][C:14]3[CH:15]=[C:16]([CH:26]=[C:27]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:28]=3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[O:18])=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][N:3]1CC1C=CC=CC=1>[Pd].C1COCC1.C(O)C>[O:41]=[S:2]1(=[O:1])[C:8]2[CH:9]=[CH:10][C:11]([O:13][C:14]3[CH:15]=[C:16]([CH:26]=[C:27]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:28]=3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[O:18])=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 1

HCID 576632163-{[1,1-dioxido-2-(phenylmethyl)-3,4-dihydro-2H-5,1,2-benzoxathiazepin-7-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 159493143-[(1,1-Dioxido-3,4-dihydro-2H-5,1,2-benzoxathiazepin-7-yl)oxy]-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamideYield 25.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

10% Palladium on carbon (30 mg) was added to 3-{[1,1-dioxido-2-(phenylmethyl)-3,4-dihydro-2H-5,1,2-benzoxathiazepin-7-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide (100 mg; 0.17 mmol) in dry THF (4 mL) and dry ethanol (4 mL) under an argon atmosphere. The reaction was degassed and placed under a hydrogen atmosphere then stirred for 24 hours at 50° C. and 20 bar. The mixture was filtered through diatomaceous earth and the filtrate evaporated. Purification via column chromatography, eluting with 50-100% ethyl acetate in isohexane, yielded a colourless oil which solidified under vacuum to give the title compound as a white foam (21 mg).

Workup

  1. customThe reaction was degassed
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. customthe filtrate evaporated
  4. customPurification via column chromatography
  5. washeluting with 50-100% ethyl acetate in isohexane
  6. customyielded a colourless oil which

Sources & evidence

ORD record
ord-d9bb9b57251f42ef990d38f84f01f097
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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