Hydrochloric Acid → (6S)-4-Nitrobenzyl 3-hydroxy-8-oxo-7-(N-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 67850

反応式

HRID 67850 の反応式
[OH:1]C1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O.[CH2:13]([C:20]1[S:26][CH:25]2[CH:22]([C:23](=[O:44])[N:24]2[C:27](=[C:41]([OH:43])[CH3:42])[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=2)=[O:29])[N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CS(Cl)(=O)=O.N1CCOCC1.BrBr.Cl>O1CCCC1.CO.N1C=CC=CC=1.C(N(CC)CC)C>[C:14]1([CH2:13][C:20]([NH:21][CH:22]2[C:23](=[O:44])[N:24]3[C:27]([C:28]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=4)=[O:29])=[C:41]([OH:43])[CH2:42][S:26][C@H:25]23)=[O:1])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

11

反応物 6

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 18950D-MannoseHCID 24408BromineHCID 31297Methanesulfonyl chlorideHCID 70503680p-Nitrobenzyl alpha-(3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-alpha-(1-hydroxyethylidene)acetate

生成物 1

HCID 67685788(6S)-4-Nitrobenzyl 3-hydroxy-8-oxo-7-(N-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate収率 71%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

Man adds triethylamine (5.68 ml) to a stirred suspension of p-nitrobenzyl α-[3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-hydroxyethylidene)acetate (9.06 g) in tetrahydrofuran (120 ml) under nitrogen atmosphere at -20° C. to give clear solution, adds methanesulfonyl chloride (1.65 ml) to the solution, stirs for 30 minutes at the same temperature, adds morpholine (1.92 ml), warms to 0° C., stirs for 5 hours, cools to -30° C. to -35° C., adds pyridine (1.54 ml) and bromine (3.12 g), stirs for 20 minutes, warms to ice-water temperatur, adds 5% hydrochloric acid (144 ml) and methanol (120 ml), stirs for 3 hours at room temperature, and lefts stand overnight at 0° C. Collection of the separated crystals in the reaction mixture by filtration gives p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephem-4-carboxylate (6.678 g). m.p. 201° C. Yield: 71%.

後処理

  1. customto give clear solution
  2. customwarms to 0° C.
  3. waitstirs for 20 minutes
  4. waitstirs for 3 hours at room temperature
  5. waitlefts stand overnight at 0° C
  6. customCollection of the separated crystals in the reaction mixture
  7. filtrationby filtration

出典と根拠

ORDレコード
ord-15ea9353f0964b50a19108f834e8cccb
出典データセット
uspto-grants-1982_08
特許番号
US04346218

関連ノート

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