Hydrochloric Acid → 3-(2-Bromo-1,3-thiazol-5-yl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561530노트

반응식

HRID 561530 반응식
[Br:1][C:2]1[S:3][C:4]([CH:7]([C:14]2[C:22]3[C:17](=[C:18]([CH2:23][S:24][CH3:25])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][C:9](OCC)=[O:10])=[CH:5][N:6]=1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)(=O)C.Cl>O1CCCC1.CCCCCCC.O1CCCC1.O>[Br:1][C:2]1[S:3][C:4]([CH:7]([C:14]2[C:22]3[C:17](=[C:18]([CH2:23][S:24][CH3:25])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][CH2:9][OH:10])=[CH:5][N:6]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 58392201Ethyl 3-(2-bromo-1,3-thiazol-5-yl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

생성물 1

HCID 583924633-(2-Bromo-1,3-thiazol-5-yl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 21263495Tetrahydrofuran heptane용매

실험 절차

A solution of 1.19 g (2.71 mmol) of the compound from Example 50A in 25 ml of tetrahydrofuran was added dropwise to 8.13 ml (8.13 mmol) of a 1N solution of diisobutylaluminum hydride in heptane/tetrahydrofuran and 25 ml of tetrahydrofuran at RT. The mixture was stirred at RT for 1 h, and the solution was mixed with ethyl acetate, water and 1N hydrochloric acid. The phases were separated, the aqueous phase was extracted three times with ethyl acetate, and the combined organic phases were washed with saturated aqueous sodium chloride solution. This was followed by drying over sodium sulfate, removal of the solid by filtration and removal of the solvents from the crude product in vacuo. Purification of the residue by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 0.73 g (68% of theory) of the title compound.

후처리

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialby drying over sodium sulfate, removal of the solid by filtration and removal of the solvents from the crude product in vacuo
  5. customPurification of the residue by preparative HPLC (mobile phase: acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-2de71e17a34f4419a8d6397abd8a0ae1
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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