Trifluoroacetic acid → HCID 90308643, compound

HRID 627748Notes

Reaction equation

HRID 627748 reaction equation
[CH3:1][C:2]1([CH3:52])[S:7](=[O:9])(=[O:8])[C@@H:6]2[CH2:10][C@H:11]([CH3:35])[O:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]5[O:31][CH:32]=[CH:33][N:34]=5)=[CH:24][N:23]=4)=[O:21])=[CH:15][C:14]=3[C@@:5]2([CH3:36])[N:4]=[C:3]1[N:37](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[NH2:37][C:3]1[C:2]([CH3:1])([CH3:52])[S:7](=[O:9])(=[O:8])[C@@H:6]2[CH2:10][C@H:11]([CH3:35])[O:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:21])[C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]5[O:31][CH:32]=[CH:33][N:34]=5)=[CH:24][N:23]=4)=[CH:15][C:14]=3[C@@:5]2([CH3:36])[N:4]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86728164HCID 86728164, compound

Product 1

HCID 90308643HCID 90308643, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution tert-butyl N-[(4aR,6S,11bR)-3,3,6,11b-tetramethyl-10-[[5-(oxazol-2-ylmethoxy)pyridine-2-carbonyl]amino]-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (19 mg, 0.026 mmol) in DCM (2 mL) was added TFA (0.049 mL, 0.642 mmol). The reaction was stirred at ambient temperature for 2 h. The reaction mixture was diluted with DCM and neutralized with saturated aqueous sodium bicarbonate. The crude product was purified by column chromatography, eluting with 20-100% (3:1 ethyl acetate/ethanol) in heptane, to provide N-((4aR,6S,11bR)-2-amino-3,3,6,11b-tetramethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-10-yl)-5-(oxazol-2-ylmethoxy)picolinamide (12 mg, 0.022 mmol, 87% yield) as a white powder. MS m/z=540.0 (M+H).

Workup

  1. customThe crude product was purified by column chromatography
  2. washeluting with 20-100% (3:1 ethyl acetate/ethanol) in heptane

Sources & evidence

ORD record
ord-98036cfaa5cc49a08eac9f0751e5f62a
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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