Pyridine → (4S,5S)-tert-butyl 4-((S)-2-(acetoxy(1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutyl)-5-((2,2-dimethylhexanamido)methyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 660399Notes

Reaction equation

HRID 660399 reaction equation
[CH3:1][C:2]([CH3:46])([CH2:42][CH2:43][CH2:44][CH3:45])[C:3]([NH:5][CH2:6][C@@H:7]1[O:11][C:10]([CH3:13])([CH3:12])[N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:8]1[CH2:21][C@H:22]([CH:26]([OH:41])[C:27]1[CH:35]=[C:34]2[C:30]([CH:31]=[N:32][N:33]2[CH2:36][CH2:37][CH2:38][O:39][CH3:40])=[CH:29][CH:28]=1)[CH:23]([CH3:25])[CH3:24])=[O:4].N1C=CC=CC=1.[NH4+].[Cl-].[CH3:55][C:56](OC(C)=O)=[O:57]>>[C:56]([O:41][CH:26]([C:27]1[CH:35]=[C:34]2[C:30]([CH:31]=[N:32][N:33]2[CH2:36][CH2:37][CH2:38][O:39][CH3:40])=[CH:29][CH:28]=1)[C@H:22]([CH:23]([CH3:25])[CH3:24])[CH2:21][C@H:8]1[C@H:7]([CH2:6][NH:5][C:3](=[O:4])[C:2]([CH3:1])([CH3:46])[CH2:42][CH2:43][CH2:44][CH3:45])[O:11][C:10]([CH3:12])([CH3:13])[N:9]1[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])(=[O:57])[CH3:55]

Participants

5

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 59630984(4S,5S)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-(hydroxy(1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59630996(4S,5S)-tert-butyl 4-((S)-2-(acetoxy(1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutyl)-5-((2,2-dimethylhexanamido)methyl)-2,2-dimethyloxazolidine-3-carboxylateYield 73%

Procedure

To a solution of (4S,5S)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-(hydroxy(1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate (32 mg, 0.05 mmol) in Ac2O (6 mL) was added pyridine (0.5 mL) dropwise. The reaction mixture was stirred at rt overnight. Satd aq NH4Cl (10 mL) was added and the mixture was extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel to give (4S,5S)-tert-butyl 4-((S)-2-(acetoxy(1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutyl)-5-((2,2-dimethylhexanamido)methyl)-2,2-dimethyloxazolidine-3-carboxylate (25 mg, 73%). MS: 687 (M+1)

Workup

  1. extractionthe mixture was extracted with EtOAc (3×15 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-75f47b2757a84e31810e3559f8a0a559
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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