Tetrahydrofuran → 2-Tert-butoxycarbonylamino-5-diazo-4-oxo-pentanoic acid methyl ester

HRID 2269308ノート

反応式

HRID 2269308 の反応式
C[Si]([CH:5]=[N+:6]=[N-:7])(C)C.C([Li])CCC.[CH3:13][O:14][C:15](=[O:29])[C@H:16]1[CH2:20][CH2:19]C(=O)[N:17]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[NH4+].[Cl-].[O:32]1CCCC1>CCCCCC>[CH3:13][O:14][C:15](=[O:29])[CH:16]([NH:17][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][C:19](=[O:32])[CH:5]=[N+:6]=[N-:7]

参加物

7

反応物 5

HCID 8028Tetrahydrofuran2 回HCID 25517Ammonium ChlorideHCID 167693TrimethylsilyldiazomethaneHCID 112650211-tert-Butyl 2-methyl (2R)-5-oxopyrrolidine-1,2-dicarboxylateHCID 178418339Butyllithium

生成物 1

HCID 540145622-Tert-butoxycarbonylamino-5-diazo-4-oxo-pentanoic acid methyl ester

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒2 回

実験手順

To a solution of trimethylsilyidiazomethane (1.24 mL of a 2M solution in hexane, 2.5 mmol) in 12 mL of tetrahydrofuran at −100° C. was added n-butyllithium (1.01 mL of a 2.5 M solution in hexane, 2.5 mmol). After stirring for 30 min, the solution was transferred via an insulated cannula to a −100° C. solution of N-BOC (D)-pyroglutamic acid methyl ester (0.50 g, 2.1 mmol) in 21 mL of tetrahydrofuran. After stirring for 20 min, the mixture was poured into saturated aqueous NH4Cl, extracted twice with ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered and concentrated, affording 0.62 g of 2-tert-butoxycarbonylamino-5-diazo-4-oxo-pentanoic acid methyl ester as a yellow oil.

後処理

  1. customwas transferred via an insulated cannula to a −100° C.
  2. stirringAfter stirring for 20 min
  3. extractionextracted twice with ethyl acetate
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-4d18130113c247deab8074de7ea2308c
出典データセット
uspto-grants-2001_12
特許番号
US06329397B1

反応ノート

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