Isobutyl chloroformate → 3-[[5-(Azidomethyl)tetrahydro-3-furanyl]thio]-4-methyl-6-[1-[[(2-methylpropoxy)carbonyl]oxy]ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

HRID 1600130ノート

反応式

HRID 1600130 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]([C:14]2[N:15]3[CH:18]([CH:19]([CH3:31])[C:20]=2[S:21][CH:22]2[CH2:26][CH:25]([CH2:27][N:28]=[N+:29]=[N-:30])[O:24][CH2:23]2)[CH:17]([CH:32]([OH:34])[CH3:33])[C:16]3=[O:35])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:37]([O:39][CH2:40][CH:41]([CH3:43])[CH3:42])=[O:38].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]([C:14]2[N:15]3[CH:18]([CH:19]([CH3:31])[C:20]=2[S:21][CH:22]2[CH2:26][CH:25]([CH2:27][N:28]=[N+:29]=[N-:30])[O:24][CH2:23]2)[CH:17]([CH:32]([O:34][C:37]([O:39][CH2:40][CH:41]([CH3:43])[CH3:42])=[O:38])[CH3:33])[C:16]3=[O:35])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 62365Isobutyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 867503233-[[5-(Azidomethyl)tetrahydro-3-furanyl]thio]-6-(1-Hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

生成物 1

HCID 536598553-[[5-(Azidomethyl)tetrahydro-3-furanyl]thio]-4-methyl-6-[1-[[(2-methylpropoxy)carbonyl]oxy]ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Using anhydrous conditions, 1.25 g of product from Example 45 in 27 ml of anhydrous tetrahydrofuran, is cooled to -78° C. under argon. 0.325 ml of isobutyl chloroformate is added, followed by 2.7 ml of lithium bis(trimethylsilyl)amide. The reaction mixture is stirred at -78° C. for 1 hour, followed by stirring at -55° C. for another hour andthen concentrated in vacuo. The residue is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane) to give 1.22 g of the desired product.

後処理

  1. stirringby stirring at -55° C. for another hour
  2. concentrationandthen concentrated in vacuo
  3. customThe residue is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-e537a856a83f40fc870a3580071583d6
出典データセット
uspto-grants-1998_04
特許番号
US05744465

反応ノート

読み込み中…