Toluene → (9S,13R)-13-methyl-13-(4,4,4-trifluorobutyl)-7,14-dioxa-2,18-dithia-5,19-diazatricyclo[14.2.1.05,9]nonadeca-1(19),10,16-triene-6,15-dione

HRID 1888318ノート

反応式

HRID 1888318 の反応式
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][S:9][C:10]2[S:11][CH:12]=[C:13]([C:15]([OH:17])=[O:16])[N:14]=2)[C@@H:5](/[CH:18]=[CH:19]/[CH2:20][C:21](O)([CH3:29])[CH2:22][CH2:23][CH2:24][C:25]([F:28])([F:27])[F:26])[CH2:4][O:3]1.C(N(CC)CC)C.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.C1(C)C=CC=CC=1>O1CCCC1>[CH3:29][C@:21]1([CH2:22][CH2:23][CH2:24][C:25]([F:27])([F:26])[F:28])[O:16][C:15](=[O:17])[C:13]2[N:14]=[C:10]([S:11][CH:12]=2)[S:9][CH2:8][CH2:7][N:6]2[C@H:5]([CH2:4][O:3][C:2]2=[O:1])[CH:18]=[CH:19][CH2:20]1

参加物

6

反応物 4

HCID 1140TolueneHCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 668588202-[(2-{(4S)-2-oxo-4-[(1E)-8,8,8-trifluoro-4-hydroxy-4-methyl-1-octenyl]-1,3-oxazolidin-3-yl}ethyl)sulfanyl]-1,3-thiazole-4-carboxylic acid

生成物 1

HCID 66857374(9S,13R)-13-methyl-13-(4,4,4-trifluorobutyl)-7,14-dioxa-2,18-dithia-5,19-diazatricyclo[14.2.1.05,9]nonadeca-1(19),10,16-triene-6,15-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the compound 45-4 (208 mg) in anhydrous tetrahydrofuran (5.0 mL) were added triethylamine (0.08 mL), 2,4,6-trichlorobenzoylchloride (0.08 mL) at 0° C. The solution was stirred for 1 Hour and then 30 minutes at room temperature. Anhydrous toluene (45.0 mL) was added to the reaction solution, which was filtrated. The obtain filtrate was added to a solution of 4-(dimethylamino)pyridine (272 mg) in anhydrous toluene (45.0 ml) with heating to reflux and the solution was allowed to return to room temperature. 1N hydrochloric acid was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (Fuji-silysia, FL60D, 75 cc, hexane:ethyl acetate=4:1) to give the title compound (less polar:83.9 mg, more polar:75.0 mg) having the following physical data.

後処理

  1. custom30 minutes
  2. customat room temperature
  3. filtrationwas filtrated
  4. additionThe obtain filtrate was added to a solution of 4-(dimethylamino)pyridine (272 mg) in anhydrous toluene (45.0 ml)
  5. temperaturewith heating
  6. temperatureto reflux
  7. customto return to room temperature
  8. addition1N hydrochloric acid was added to the reaction solution, which
  9. extractionwas extracted with ethyl acetate
  10. washThe organic layer was washed with water and brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe obtained residue was purified by column chromatography on silica gel (Fuji-silysia, FL60D, 75 cc, hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-bc01021b95464ebfa83703735bb1663b
出典データセット
uspto-grants-2013_08
特許番号
US08501793B2

反応ノート

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