Ammonia → HCID 69651157, compound

HRID 1743264Notes

Reaction equation

HRID 1743264 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]1([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])[CH2:24][CH2:23]2)[C:16](=[O:17])[N:15]2[C@@H:11]([S:12][CH2:13][C@H:14]2[C:18](OC)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:37]>>[C:1]([O:5][C:6]([NH:8][C@@:9]1([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:36])[CH3:35])=[O:29])[CH2:24][CH2:23]2)[C:16](=[O:17])[N:15]2[C@@H:11]([S:12][CH2:13][C@H:14]2[C:18]#[N:37])[CH2:10]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 91250266HCID 91250266, compound

Product 1

HCID 69651157HCID 69651157, compound

Procedure

153 mg of methyl (3R,6S,7aS)-6-tert-butoxycarbonylamino-5-oxo-6-[1-(2-trimethylsilanylethoxycarbonyl)piperidin-4-yl]hexahydropyrrolo[2,1-b]thiazole-3-carboxylate were dissolved at 0° C. in 30 ml of ammonia-saturated methanol. The mixture was allowed to reach room temperature over the course of 5 h, and then the solvents were removed in vacuo. The residue was taken up in 5 ml of THF, and 100 μl of triethylamine and 60 μl of trifluoroacetic anhydride were successively added. The mixture was stirred at room temperature for 2 h. It was then partitioned between 60 ml of 0.5 M HCl and 60 ml of ethyl acetate. The aqueous phase was extracted twice with 20 ml of ethyl acetate each time, and the combined organic phases were washed once with 30 ml of saturated sodium bicarbonate solution. After drying with MgSO4, the solvents were removed in vacuo. The residue was chromatographed on silica gel.

Workup

  1. customto reach room temperature over the course of 5 h
  2. customthe solvents were removed in vacuo
  3. addition100 μl of triethylamine and 60 μl of trifluoroacetic anhydride were successively added
  4. customIt was then partitioned between 60 ml of 0.5 M HCl and 60 ml of ethyl acetate
  5. extractionThe aqueous phase was extracted twice with 20 ml of ethyl acetate each time
  6. washthe combined organic phases were washed once with 30 ml of saturated sodium bicarbonate solution
  7. dry with materialAfter drying with MgSO4
  8. customthe solvents were removed in vacuo
  9. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-d9f76875b70e4a2883ae5f45a9cc4df9
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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