(1R,2S,7R,8S)-5-(7-azidomethyl-1,1-dioxo-1,4-dihydro-1lambda6 thieno[2,3-e][1,2,4]thiadiazin-3-yl)-3-(4-fluoro-benzyl)-6-hydroxy-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one → (1R,2S,7R,8S)-5-(7-aminomethyl-1,1-dioxo-1,4-dihydro-1lambda6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-3-(4-fluoro-benzyl)-6-hydroxy-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one

HRID 421513Notes

Reaction equation

HRID 421513 reaction equation
[N:1]([CH2:4][C:5]1[C:13]2[S:12](=[O:15])(=[O:14])[N:11]=[C:10]([C:16]3[C:17](=[O:36])[N:18]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[C@@H:19]4[C@H:24]([C:25]=3[OH:26])[C@@H:23]3[CH2:27][C@H:20]4[CH2:21][CH2:22]3)[NH:9][C:8]=2[S:7][CH:6]=1)=[N+]=[N-]>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:1][CH2:4][C:5]1[C:13]2[S:12](=[O:14])(=[O:15])[N:11]=[C:10]([C:16]3[C:17](=[O:36])[N:18]([CH2:28][C:29]4[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=4)[C@@H:19]4[C@H:24]([C:25]=3[OH:26])[C@@H:23]3[CH2:27][C@H:20]4[CH2:21][CH2:22]3)[NH:9][C:8]=2[S:7][CH:6]=1

Participants

5

Reactant 1

HCID 136395906(1R,2S,7R,8S)-5-(7-azidomethyl-1,1-dioxo-1,4-dihydro-1lambda6 thieno[2,3-e][1,2,4]thiadiazin-3-yl)-3-(4-fluoro-benzyl)-6-hydroxy-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one

Product 1

HCID 136395907(1R,2S,7R,8S)-5-(7-aminomethyl-1,1-dioxo-1,4-dihydro-1lambda6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-3-(4-fluoro-benzyl)-6-hydroxy-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-oneYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,2S,7R,8S)-5-(7-azidomethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-3-(4-fluoro-benzyl)-6-hydroxy-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one (0.10 g, 0.19 mmol) in ethanol (6 mL) and ethyl acetate (3 mL) was added 10% palladium on carbon (10 mg). The mixture was degassed and stirred under an atmosphere of hydrogen gas (balloon) overnight. The resulting mixture was diluted with N,N-dimethylformamide (10 mL) and filtered through a pad of Celite. The organic was concentrated in vacuo to afford the crude product, (1R,2S,7R,8S)-5-(7-aminomethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-3-(4-fluoro-benzyl)-6-hydroxy-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one (95 mg, 0.19 mmol, 100%), which was used in the next step without further purification.

Workup

  1. customThe mixture was degassed
  2. additionThe resulting mixture was diluted with N,N-dimethylformamide (10 mL)
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe organic was concentrated in vacuo

Sources & evidence

ORD record
ord-13044eecb89c4f4eb982b3c678bebf6c
Source dataset
uspto-grants-2012_01
Patent number
US08097613B2

Reaction notes

Loading…