Trifluoroacetic acid → HCID 62705267, compound

HRID 1778497Notes

Reaction equation

HRID 1778497 reaction equation
[CH2:1]([C:5]([NH:16]C(OC(C)(C)C)=O)([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2][CH:3]=[CH2:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:16][C:5]([CH2:1][CH2:2][CH:3]=[CH2:4])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86663717Diethyl 2-(but-3-enyl)-2-(tert-butoxycarbonylamino)malonate

Product 1

HCID 62705267HCID 62705267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 2-but-3-enyl-2-(tert-butoxycarbonylamino)propanedioate 81b (14.5 g, 4.4 mmol) in DCM (30 mL) was added TFA (10 mL), The mixture was stirred at room temperature for 16 h, quenched with saturated NaHCO3 (50 mL) and then extracted with DCM (150 mL) two times, washed with saturated NaHCO3 (100 mL) three times, dried over anhydrous sodium sulfate and concentrated in vacuo to afford diethyl 2-amino-2-but-3-enyl-propanedioate as a crude product (9.5 g, 94%), which was used for next step without further purification. MS: calc'd (MH+) 230, measured (MH+) 230.

Workup

  1. customquenched with saturated NaHCO3 (50 mL)
  2. extractionextracted with DCM (150 mL) two times
  3. washwashed with saturated NaHCO3 (100 mL) three times
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7b5682be8ab4258aa8f92e92c0113b5
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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