Trifluoroacetic acid → (4aR,11bR)-3,3,11b-trimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazine-2,10-diamine

HRID 627626ノート

反応式

HRID 627626 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:27][CH2:26][CH2:25][C@H:8]3[S:9](=[O:24])(=[O:23])[C:10]([CH3:22])([CH3:21])[C:11]([NH:13]C(=O)OC(C)(C)C)=[N:12][C@:7]3([CH3:28])[C:6]=2[CH:29]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:21][C:10]1([CH3:22])[S:9](=[O:23])(=[O:24])[C@@H:8]2[CH2:25][CH2:26][O:27][C:5]3[CH:4]=[CH:3][C:2]([NH2:1])=[CH:29][C:6]=3[C@@:7]2([CH3:28])[N:12]=[C:11]1[NH2:13]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 90307362tert-butyl ((4aR,11bR)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate2 回

生成物 1

HCID 90307372(4aR,11bR)-3,3,11b-trimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazine-2,10-diamine収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of tert-butyl ((4aR,11bR)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (intermediate 19) (308 mg, 0.727 mmol) in DCM (5.5 ml) was treated with trifluoroacetic acid (2.70 ml, 36.4 mmol) for 15 min. The mixture was concentrated, redissolved in DCM, diluted with water and free-based with a saturated solution of NaHCO3. The mixture was extracted with DCM, organic extract was washed with brine, filtered through pad of celite and concentrated to afford (4aR,11bR)-3,3,11b-trimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazine-2,10-diamine (180 mg, 0.557 mmol, 77% yield) as an off-white solid. LC/MS (ESI+) m/z=324.2 (M+H).

後処理

  1. concentrationThe mixture was concentrated
  2. dissolutionredissolved in DCM
  3. additiondiluted with water and free-based with a saturated solution of NaHCO3
  4. extractionThe mixture was extracted with DCM
  5. extractionorganic extract
  6. washwas washed with brine
  7. filtrationfiltered through pad of celite
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0beb2f907b364f8f8daa29b052a47418
出典データセット
uspto-grants-2016_04
特許番号
US09309263B2

反応ノート

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