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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
ノート
印刷プレビュー

反応式

HRID 1684633 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-487f3965e776490b9ce9570a88f28f26
出典データセット
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05641789

反応ノート

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