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2,2,2-Trifluoroethyl formate → methyl(7R)-14-cyclohexyl-7-{methyl[2-(methylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 421945
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HRID 421945 반응식
[NH2:1][CH2:2][CH2:3][N:4]([CH3:34])[C@@H:5]1[CH2:12][N:11]2[C:13]3[CH:14]=[C:15]([C:26]([O:28][CH3:29])=[O:27])[CH:16]=[CH:17][C:18]=3[C:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:10]2[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[O:7][CH2:6]1.[CH:35](OCC(F)(F)F)=O>C1COCC1>[CH:20]1([C:19]2[C:18]3[CH:17]=[CH:16][C:15]([C:26]([O:28][CH3:29])=[O:27])=[CH:14][C:13]=3[N:11]3[C:10]=2[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[O:7][CH2:6][C@H:5]([N:4]([CH3:34])[CH2:3][CH2:2][NH:1][CH3:35])[CH2:12]3)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1
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참가 물질

4

반응물 2

HCID 1416812,2,2-Trifluoroethyl formateHCID 66674669methyl(7R)-7-[(2-aminoethyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

생성물 1

HCID 66675300methyl(7R)-14-cyclohexyl-7-{methyl[2-(methylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate수율 40%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution (0.1 M) of methyl(7R)-7-[(2-aminoethyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate in THF was treated dropwise with 2,2,2-trifluoroethyl formate (1.5 eq.) and stirred overnight at RT. The volatiles were removed in vacuo and the residue dissolved (0.1 M) in THF and treated dropwise with BH3-DMS complex (2M in THF; 5 eq.). The resulting solution was stirred at RT for 3 h. The reaction was quenched by the careful addition of HCl/MeOH (1.25 M) and the resulting solution heated to dryness. The residue was then partitioned between sat. aq. NaHCO3 and EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude was purified by FC (EtOAc/MeOH 99.5:0.5+1% NEt3) to afford the product (40%). (ES+) m/z 476 (M+H)+.

후처리

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved (0.1 M) in THF
  3. stirringThe resulting solution was stirred at RT for 3 h
  4. customThe reaction was quenched by the careful addition of HCl/MeOH (1.25 M)
  5. temperaturethe resulting solution heated to dryness
  6. customThe residue was then partitioned between sat. aq. NaHCO3 and EtOAc
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude was purified by FC (EtOAc/MeOH 99.5:0.5+1% NEt3)

출처 및 근거

ORD 기록
ord-7ee733c484ba419bb2ce3a58c5ce1203
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08101595B2

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