Ethyl Acetate → HCID 21426467、化合物

HRID 258780ノート

反応式

HRID 258780 の反応式
[C:1]([O:7][CH2:8]I)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[K].[C:11]([C:14]1[N:15]2[CH:18]([S:19][CH2:20][C:21]=1[CH2:22][S:23][C:24]1[S:28][C:27]([CH3:29])=[N:26][N:25]=1)[CH:17]([NH:30][C:31](=[O:39])[CH2:32][C:33]1[S:34][C:35](=[O:38])[S:36][CH:37]=1)[C:16]2=[O:40])([OH:13])=[O:12].C(OCC)(=O)C>CN(C)C=O.O>[CH3:29][C:27]1[S:28][C:24]([S:23][CH2:22][C:21]2[CH2:20][S:19][CH:18]3[N:15]([C:16](=[O:40])[CH:17]3[NH:30][C:31](=[O:39])[CH2:32][C:33]3[S:34][C:35](=[O:38])[S:36][CH:37]=3)[C:14]=2[C:11]([O:13][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:12])=[N:25][N:26]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 104401Iodomethyl pivalateHCID 5462222PotassiumHCID 21426458HCID 21426458、化合物

生成物 1

HCID 21426467HCID 21426467、化合物収率 47.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Iodomethyl pivalate (2.66 g.) is added to a suspension of the potassium salt of 2-carboxy-3-[(2-methyl-1,3,4-thiadiazol-5-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo-[4.2.0]oct-2-ene (5.18 g.) in dimethyl formamide (100 cc.) cooled to 0° C. The reaction mixture is stirred for 10 minutes at 5° C.; it becomes limpid and is poured into a decanting funnel containing ethyl acetate (100 cc.) and water (200 cc.). The organic phase is washed with a saturated sodium bicarbonate solution (100 cc.) and then with a saturated sodium chloride solution (100 cc.). The organic phase is dried over sodium sulphate, treated with decolourising charcoal, filtered and concentrated to dryness under reduced pressure (20 mm Hg). The residue (5 g.) is chromatographed on silica (80 g.). A product (4.5 g.) is eluted with a 70-30 by volume mixture of ethyl acetate and cyclohexane, and is crystallised from a mixture of ethyl acetate and cyclohexane (50-50 by volume) (60 cc.). 3-[(2-Methyl-1,3,4-thiadiazol-5-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-2-pivaloyloxymethoxycarbonyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (3 g.) is thus obtained as white crystals m.p. approximately 110° C.

後処理

  1. additionis poured into a decanting funnel
  2. washThe organic phase is washed with a saturated sodium bicarbonate solution (100 cc.)
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. additiontreated with decolourising charcoal
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (20 mm Hg)
  7. customThe residue (5 g.) is chromatographed on silica (80 g.)
  8. washA product (4.5 g.) is eluted with a 70-30 by volume mixture of ethyl acetate and cyclohexane
  9. customis crystallised from a mixture of ethyl acetate and cyclohexane (50-50 by volume) (60 cc.)

出典と根拠

ORDレコード
ord-eee4f3dbadeb471290052db97371159d
出典データセット
uspto-grants-1977_07
特許番号
US04034090

反応ノート

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