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 627626노트

반응식

HRID 627626 반응식
[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]

참가 물질

4

반응물 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)carbamate2회

생성물 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-diamine수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0beb2f907b364f8f8daa29b052a47418
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309263B2

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