Hydrochloric Acid → HCID 178460821、化合物

HRID 461979ノート

反応式

HRID 461979 の反応式
Br[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C([N:39]1[C:43](=[S:44])[NH:42][N:41]=[N:40]1)C.[CH2:45](N(CC)CC)[CH3:46].Cl>O1CCCC1.[Cl-].[Na+].O.C(OCC)(=O)C.O>[CH2:45]([CH:2]([S:44][C:43]1[NH:42][N:41]=[N:40][N:39]=1)[C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH3:46]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 70592080HCID 70592080、化合物HCID 178463196HCID 178463196、化合物

生成物 1

HCID 178460821HCID 178460821、化合物

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of diphenylmethyl 3-bromomethyl-7β-(2-thienylacetamido)-ceph-3-em-4-carboxylate (11.67 g) and 1-ethyltetrazoline-5-thione (2.6g) in dry tetrahydrofuran (150ml) was stirred at 0° and a solution of triethylamine (2.8ml) in tetrahydrofuran (25ml) was added, dropwise, over 5 minutes. The resulting suspension was stirred for a further 25 minutes, during which time the temperature was allowed to rise to ca. 20°, and was then added, over 5 minutes, to a stirred mixture of 2N-hydrochloric acid (50ml), water (350ml), brine (350ml), and ethyl acetate (600ml). The organic phase was separated, and washed with 2N-hydrochloric acid, saturated sodium bicarbonate, water, and brine, and dried and evaporated to a foam (11.71g). A solution of this foam in benzene (25ml) was purified by chromatography on kieselgel (200g), with benzene:ethyl acetate = 5:1 as eluant. Appropriate fractions were combined and the solvents evaporated in vacuo. The residue was dissolved in methylene dichloride, and the solution run into petroleum ether to give the ester as a pale-yellow, amorphous solid (8.585g, 68 %); [α]D 23 - 131° (c 0.97. CHCl3); λmax. (EtOH) 264 nm (ε 7,300), τ (CDCl3) values include 4.12 (7-H, dd, J 5 and 9 Hz.), 5.04 (6-H, d, J 5 Hz.), 5.83 (CH3CH2 -,q, J 7 Hz.), and 8.57 (CH3CH2 -, t, J 7 Hz.).

後処理

  1. customto rise to ca. 20°
  2. customThe organic phase was separated
  3. washwashed with 2N-hydrochloric acid, saturated sodium bicarbonate, water, and brine
  4. customdried
  5. customevaporated to a foam (11.71g)
  6. customA solution of this foam in benzene (25ml) was purified by chromatography on kieselgel (200g), with benzene
  7. customthe solvents evaporated in vacuo
  8. dissolutionThe residue was dissolved in methylene dichloride

出典と根拠

ORDレコード
ord-974459a45bee48f79ad52b9856ab6fca
出典データセット
uspto-grants-1977_12
特許番号
US04064346

反応ノート

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