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

HRID 2269308노트

반응식

HRID 2269308 반응식
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]

참가 물질

7

반응물 5

HCID 8028Tetrahydrofuran2회HCID 25517Ammonium ChlorideHCID 167693TrimethylsilyldiazomethaneHCID 112650211-tert-Butyl 2-methyl (2R)-5-oxopyrrolidine-1,2-dicarboxylateHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8058Hexane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d18130113c247deab8074de7ea2308c
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06329397B1

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