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

HRID 2269308Notes

Reaction equation

HRID 2269308 reaction equation
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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4d18130113c247deab8074de7ea2308c
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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