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Methanol → (+/-)-C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-trans-2-methyl-4-oxochroman-3-ylmethyl]phenyl}methanesulfonamide

HRID 1684633
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HRID 1684633 반응식
[F:1][C:2]([F:39])([F:38])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][C:27]4[S:28][C:29]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:30]=5[N:31]=4)[CH:21]=3)[O:16][C:15]=2[CH3:37])[CH:8]=1)(=[O:5])=[O:4].CO>O1CCCC1.ClCCl>[F:39][C:2]([F:1])([F:38])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C@@H:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][C:27]4[S:28][C:29]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:30]=5[N:31]=4)[CH:21]=3)[O:16][C@H:15]2[CH3:37])[CH:8]=1)(=[O:5])=[O:4]
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참가 물질

5

반응물 2

HCID 887MethanolHCID 19039946C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-2-methyl-4-oxo-4H-chromen-3-ylmethyl]phenyl}methanesulfonamide

생성물 1

HCID 131720055(+/-)-C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-trans-2-methyl-4-oxochroman-3-ylmethyl]phenyl}methanesulfonamide수율 54%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

To a stirred suspension of 2.59 g (4.48 mmole) product from Example 127 in 100 mL tetrahydrofuran was added dropwise 9 mL (9.40 mmole) UB(sec-butyl)3H (1M in THF, L-Selectride®) at -78° C. The mixture was stirred for 2 hours, then quenched with 5% ammonium chloride. The mixture was poured into water, acidified to ph 1-4 with 1N HCl, and extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine and dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 2.5% methanol in dichloromethane afforded 1.4 g (54%) of the title product as a solid, mp 183°-185° C. Analysis calculated for C26H20N2S2O5F4 : C, 53.79; H, 3.47; N, 4.83. Found: C, 53.25; H, 3.23; N, 4.45.

후처리

  1. additionwas added dropwise 9 mL (9.40 mmole) UB(sec-butyl)3H (1M in THF, L-Selectride®) at -78° C
  2. customquenched with 5% ammonium chloride
  3. additionThe mixture was poured into water
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give an oil

출처 및 근거

ORD 기록
ord-487f3965e776490b9ce9570a88f28f26
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05641789

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