Ammonium formate → HCID 57827775, compound

HRID 1842153Notes

Reaction equation

HRID 1842153 reaction equation
C([O-])=O.[NH4+].[C:5]([O:9][C:10]([N:12]([C:20]1[S:21][CH2:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][C@:24]2([C:29]2[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([N:36]=[N+]=[N-])[CH:30]=2)[N:25]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:11])([CH3:8])([CH3:7])[CH3:6]>CO.[Zn]>[C:16]([O:15][C:13]([N:12]([C:20]1[S:21][CH2:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][C@:24]2([C:29]2[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([NH2:36])[CH:30]=2)[N:25]=1)[C:10]([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11])=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57827627HCID 57827627, compound

Product 1

HCID 57827775HCID 57827775, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (12.4 mg) and zinc (3.86 mg) were added to a solution of (±)-N,N-bis(t-butoxycarbonyl) [(4aR*,7aS*)-7a-(3-azido-5-chlorophenyl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl]amine (20.0 mg) in methanol (2 mL). The mixture was stirred at room temperature overnight, and then the excess of methanol was evaporated under reduced pressure. The residue was diluted with ethyl acetate, and the organic layer was washed with an ammonium chloride solution. The solvent was evaporated under reduced pressure and the residue was purified by pTLC to obtain the title compound (13.0 mg).

Workup

  1. customthe excess of methanol was evaporated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washthe organic layer was washed with an ammonium chloride solution
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by pTLC

Sources & evidence

ORD record
ord-a81202e536aa43b79f70b34aa40fc5e6
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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