Formic Acid → HCID 86693809, compound

HRID 514665Notes

Reaction equation

HRID 514665 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=O.C(OCC)(=O)C>O>[CH2:1]([O:8][C:9]([N:11]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8857Ethyl AcetateHCID 86693810HCID 86693810, compound

Product 1

HCID 86693809HCID 86693809, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To tert-butyl 3-{N-benzyloxycarbonyl-N-(ethoxycarbonylmethyl)amino}propionate (500 mg, 1.37 mmol) was added formic acid (2.5 mL, 66.3 mmol), followed by stirring at an outer temperature set of 40° C. for 3 hours. After leaving to be cooled, to the reaction mixture were added ethyl acetate (10 mL) and water (10 mL), and the organic layer was collected by separation. To the aqueous layer was added ethyl acetate (10 mL), the organic layer was collected by separation, and then the organic layer was combined, washed with saturated brine (10 mL), then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained concentrated residue was dried at room temperature under reduced pressure to obtain 421 mg (yield 99%) of a title compound as colorless oil.

Workup

  1. customAfter leaving
  2. temperatureto be cooled, to the reaction mixture
  3. customthe organic layer was collected by separation
  4. additionTo the aqueous layer was added ethyl acetate (10 mL)
  5. customthe organic layer was collected by separation
  6. washwashed with saturated brine (10 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained concentrated residue was dried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-bdabb3d8525a4bfbb9eef0c47b3625ec
Source dataset
uspto-grants-2015_08
Patent number
US09108915B2

Reaction notes

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