Trifluoroacetic acid → (4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrile

HRID 529486Notes

Reaction equation

HRID 529486 reaction equation
FC(F)(F)C(O)=O.[C:8]([C@H:10]1[N:20]2[C@@H:14]([S:15][CH2:16][CH2:17][C@H:18]([NH:22]C(=O)OC(C)(C)C)[C:19]2=[O:21])[CH2:13][CH2:12][CH2:11]1)#[N:9]>C(Cl)Cl>[NH2:22][C@H:18]1[CH2:17][CH2:16][S:15][C@H:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:8]#[N:9])[N:20]2[C:19]1=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86706201tert-butyl (4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

Product 1

HCID 68292315(4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrileYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.15 mL) was added to a 0° C. solution of tert-butyl (4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (36 mg, 0.11 mmol) in DCM (0.35 mL). The reaction mixture was then stirred at rt for 45 min. The reaction mixture was concentrated. The residue was partitioned between EtOAc and saturated aqueous NaHCO3. The EtOAc was isolated, dried over MgSO4, filtered and concentrated give (4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrile (15 mg, 0.067 mmol, 60% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. customThe EtOAc was isolated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eb5a4c40e1c947288cf3ae3deabd9079
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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