Water → ethyl gamma-(N-carbobenzoxy)amino-gamma-cyanobutanoate

HRID 1292365Notes

Reaction equation

HRID 1292365 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][C@@H:7]([C:19](=O)[NH2:20])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH3:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C1COCC1.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH:7]([C:19]#[N:20])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 18637511HCID 18637511, compound

Product 1

HCID 53725343ethyl gamma-(N-carbobenzoxy)amino-gamma-cyanobutanoate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of Cbz-isoglutamine ethyl ester (15.42 g, 50 mmol) and pyridine (8.48 mL, 105 mmol) in 360 mL of anhydrous THF at 0° C. was added dropwise a solution of trifluoroacetic anhydride (7.77 mL, 55 mmol) in 40 mL of THF, at such a rate to maintain a temperature of 0°-5° C. for 1-2 hours or until reaction was complete as evidenced by TLC (5% H2O/94% CH3CN/1% HOAc; Cu(OAc)2 stain.

Workup

  1. temperatureat such a rate to maintain a temperature of 0°-5° C. for 1-2 hours
  2. customuntil reaction

Sources & evidence

ORD record
ord-142a970d2a8541bda9c7ecfc35773cb5
Source dataset
uspto-grants-1998_05
Patent number
US05756685

Reaction notes

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