Dimethylformamide → Tert-butyl[4-(2,6-dichloropyrid-4-ylmethyl)-5-oxoperhydro-1,4-thiazepin-6-yl]carbamate

HRID 1986541ノート

反応式

HRID 1986541 の反応式
[H-].[Na+].CN(C=O)C.[O:8]=[C:9]1[CH:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][S:13][CH2:12][CH2:11][NH:10]1.Br[CH2:25][C:26]1[CH:31]=[C:30]([Cl:32])[N:29]=[C:28]([Cl:33])[CH:27]=1>O.CCOC(C)=O>[Cl:33][C:28]1[CH:27]=[C:26]([CH2:25][N:10]2[C:9](=[O:8])[CH:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH2:14][S:13][CH2:12][CH2:11]2)[CH:31]=[C:30]([Cl:32])[N:29]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27818294-(Bromomethyl)-2,6-dichloropyridineHCID 15591256(Hexahydro-5-oxo-1,4-thiazepin-6-yl)carbamic acid, (1,1-dimethylethyl) ester

生成物 1

HCID 57722295Tert-butyl[4-(2,6-dichloropyrid-4-ylmethyl)-5-oxoperhydro-1,4-thiazepin-6-yl]carbamate収率 23%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

121 mg of sodium hydride as a 60% suspension in oil (3.05 mmol) are introduced at room temperature into a 50 ml round-bottomed flask, with stirring and under an argon atmosphere, containing 20 ml of DMF and 500 mg of 26 (2.03 mmol). The medium is stirred for 1 hour and 489 mg (2.03 mmol) of 4-bromomethyl-2,6-dichloropyridine are then added. The medium is stirred for 3 hours, 50 ml of EtOAc and 50 ml of water are added to the reaction medium and, after separation of the phases by settling, the organic phase is washed once with 50 ml of water. The organic phase is dried, filtered and then evaporated to dryness. 1.5 g of crude product are recovered, which product is chromatographed on a silica cartridge (20 g) with an 80/20 heptane/EtOAc mixture. 190 mg of product 36 are recovered (yield=23%).

後処理

  1. stirringThe medium is stirred for 1 hour
  2. stirringThe medium is stirred for 3 hours
  3. customafter separation of the phases
  4. washthe organic phase is washed once with 50 ml of water
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated to dryness
  8. custom1.5 g of crude product are recovered
  9. customwhich product is chromatographed on a silica cartridge (20 g) with an 80/20 heptane/EtOAc mixture
  10. custom190 mg of product 36 are recovered (yield=23%)

出典と根拠

ORDレコード
ord-9184b3e7cb0c4aa2a5c6468e5d6c5614
出典データセット
uspto-grants-2009_06
特許番号
US07550453B2

反応ノート

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