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Sodium Chloride → n-Hexanoyloxymethyl 7-(2-[2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate

HRID 364506
ノート
印刷プレビュー

反応式

HRID 364506 の反応式
P(Cl)(Cl)Cl.[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:38][O:39][CH3:40])[C:12]([NH:14][CH:15]2[C:36](=[O:37])[N:17]3[C:18]([C:24]([O:26][CH2:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:25])=[C:19]([Cl:23])[CH2:20][S:21](=O)[C@H:16]23)=[O:13])[N:10]=1.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:38][O:39][CH3:40])[C:12]([NH:14][CH:15]2[C:36](=[O:37])[N:17]3[C:18]([C:24]([O:26][CH2:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:25])=[C:19]([Cl:23])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 131712436n-Hexanoyloxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate-1-oxide

生成物 1

HCID 131712435n-Hexanoyloxymethyl 7-(2-[2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate収率 27.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Phosphorus trichloride (210 mg.) was added to a solution of n-hexanoyloxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate-1-oxide (syn-isomer: 570 mg.) in dry dimethylformamide (10 ml.) at -30° C., and stirred at -20° to -30° C. for 50 minutes. 10% Aqueous solution (50 ml.) of sodium chloride was added to the resultant solution, adjusted to pH 8.0 with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue (560 mg.) was purified with column chromatography on silica gel (20 g.) (eluent:ethyl acetate), and the resultant residue (180 mg.) was pulverized with n-hexane (10 ml.) and diethyl ether (5 ml.) to give n-hexanoyloxymethyl 7-[2-(2-amino-4-thiazolyl)- 2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn-isomer: 150 mg.) over magnesium sulfate and then concentrated under reduced pressure. The residue was pulverized with diisopropyl ether to give 7-[2-{2-(2,2,2-trifluoroacetamido)-4-thiazolyl}-2-methoxyiminoacetamido]-2,3-dimethyl-3-cephem-4-carboxylic acid (syn isomer, 0.9 g.).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue (560 mg.) was purified with column chromatography on silica gel (20 g.) (eluent:ethyl acetate)

出典と根拠

ORDレコード
ord-6f290c5c7e794cf0a5a2d0a25cb24ea9
出典データセット
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04604456

反応ノート

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