Hydrochloric Acid → HCID 178460821, 화합물

HRID 918597노트

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HRID 918597 반응식
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]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 70592080HCID 70592080, 화합물HCID 178463196HCID 178463196, 화합물

생성물 1

HCID 178460821HCID 178460821, 화합물

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

A solution of diphenylmethyl 3-bromomethyl-7β-(2-thienylacetamido)-ceph-3-em-4-carboxylate (11.67g) 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]D23 - 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 --, 9, J 7 Hz.), and 8.57 (CH3CH2 --, t, J 7 Hz.).

후처리

  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

출처 및 근거

ORD 기록
ord-aa592e85f83a459584932978a4b7f6a6
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03971778

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