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Triethylamine → (6R,7R)-3-[(1-acetamidotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 483029
ノート
印刷プレビュー

反応式

HRID 483029 の反応式
[NH2:1][C@@H:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]3[N:15]([NH:16][C:17](=[O:19])[CH3:18])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.C(N(CC)CC)C.[C:32]([NH:51][C:52]1[S:53][CH:54]=[C:55](/[C:57](=[N:70]/[O:71][CH3:72])/[C:58](ON2C3C=CC=CC=3N=N2)=[O:59])[N:56]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:32]([NH:51][C:52]1[S:53][CH:54]=[C:55](/[C:57](=[N:70]/[O:71][CH3:72])/[C:58]([NH:1][C@@H:2]2[C:23](=[O:24])[N:4]3[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]4[N:15]([NH:16][C:17](=[O:19])[CH3:18])[N:14]=[N:13][N:12]=4)[CH2:7][S:8][C@H:3]23)=[O:59])[N:56]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 704535287beta-amino-3-[(1-acetamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acidHCID 88675991benzotriazol-1-yl (2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate

生成物 1

HCID 13261994(6R,7R)-3-[(1-acetamidotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 7β-amino-3-[(1-acetamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (0.450 g, 1.21 mmol), triethylamine (0.245 mg, 2.42 mmol) and dichloromethane (10 ml) was stirred at room temperature for 10 minutes. To the mixture was added 1-benzotriazolyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetate (0.678 g, 1.21 mmol) and allowed to react at 5° C. for 17 hours. The dichloromethane was removed by evaporation. Water (10 ml) and triethylamine (0.5 ml) were added to the residue. The aqueous layer was separated, washed with ethyl acetate (5 ml) and adjusted to pH 3.5 with citric acid. Precipitated substance was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated. The residue was treated with ether and filtered to give pale yellow powder of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1-acetamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem- 4-carboxylic acid (0.790 g, 92%), mp 167°-170° C. (decomposition).

後処理

  1. customto react at 5° C. for 17 hours
  2. customThe dichloromethane was removed by evaporation
  3. additionWater (10 ml) and triethylamine (0.5 ml) were added to the residue
  4. customThe aqueous layer was separated
  5. washwashed with ethyl acetate (5 ml)
  6. customPrecipitated substance
  7. extractionwas extracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. additionThe residue was treated with ether
  12. filtrationfiltered

出典と根拠

ORDレコード
ord-0848abbdd3bc4e1da1c4109145d7ec52
出典データセット
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04576938

反応ノート

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