HCID 57504899, compound → HCID 57504900, compound

HRID 2060768Notes

Reaction equation

HRID 2060768 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([C@:10]23[CH2:19][CH2:18][O:17][CH2:16][CH:15]2[CH2:14][S:13][C:12]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:11]3)[CH:7]=[CH:8][CH:9]=1)=[N+]=[N-]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([C@:10]23[CH2:19][CH2:18][O:17][CH2:16][CH:15]2[CH2:14][S:13][C:12]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[N:11]3)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 57504899HCID 57504899, compound

Product 1

HCID 57504900HCID 57504900, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl (8aS)-8a-(3-azidophenyl)-4,4a,5,7,8,8a-hexahydropyrano[4,3-d][1,3]thiazin-2-ylcarbamate (0.398 g, 1.02 mmol) and palladium on carbon −10% by weight (0.200 g) in ethanol (25 mL) is purged with nitrogen then hydrogen. The reaction is stirred at room temperature under hydrogen (30 psi) for 2 h. Na2SO4 is added to the reaction mixture and it is filtered through diatomaceous earth, using methanol to rinse the filter cake. The solvent is removed under reduced pressure to give the title compound (0.361 g, 97%). ES/MS m/e: 364 (M+1).

Workup

  1. customis purged with nitrogen
  2. additionNa2SO4 is added to the reaction mixture and it
  3. filtrationis filtered through diatomaceous earth
  4. washto rinse the filter cake
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-2a3ee9df17f84f019cb3fe48a9a9ad01
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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