Triphenylphosphine → Methyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate

HRID 1289244

Reaction equation

HRID 1289244 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:16][CH2:17][C:18](=O)[NH2:19])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)(Cl)(Cl)Cl>[CH2:9]([O:8][C:6]([NH:5][C@@H:4]([CH2:16][CH2:17][C:18]#[N:19])[C:3]([O:2][CH3:1])=[O:21])=[O:7])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 7020255Z-Gln-ome

Product 1

HCID 11000307Methyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of N-benzyloxycarbonyl-L-glutamine methyl ester (25 g) in THF (500 ml) was added dropwise to a stirred solution of triphenylphosphine (44.5 g) in carbon tetrachloride (1 L). The mixture was heated to 50° C. for 2 hours. The mixture was evaporated. The resultant oil was triturated in ethyl acetate. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatogaphy using a 1:1 mixture of hexane and ethyl acetate as eluant. There was thus obtained methyl (2S)-2-benzyloxycarbonylarnino-4-cyanobutyrate (19.38 g, 83%).

Workup

  1. customThe mixture was evaporated
  2. customThe resultant oil was triturated in ethyl acetate
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatogaphy
  6. additiona 1:1 mixture of hexane and ethyl acetate as eluant

Sources & evidence

ORD record
ord-ebe61e5660a14d72aaeb847aa9d66948
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Linked notes

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