Formic Acid → HCID 72436296, compound

HRID 459140Notes

Reaction equation

HRID 459140 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1)[CH3:2].C(O)=[O:19]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:15][CH3:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13](=[O:19])[CH3:14])=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 58822937HCID 58822937, compound

Product 1

HCID 72436296HCID 72436296, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To (2S)-3-(4-Ethynyl-phenyl)-2-methoxy-propionic acid ethyl ester (36 Mg, 0.15 mmol) (Example 29, Step A) were added 4 ml of formic acid. The solution was stirred for 1 hour at 100° C. and then cooled to room temperature. The mixture was taken up with methylene chloride and the solution was washed with water, sodium carbonate, and water, dried (MgSO4) and the solvent was evaporated under vacuum. Obtained a brown liquid (0.035 g, 95%). 1H-NMR (200.15 MHz, CDCl3): δ 7.43 (d, 1H, J=73), 7.12 (d, 1H, J=7.3), 4.18 (q, 2H, J=7.0), 3.97 (dd, 1H, J=7.3, 5.6), 3.32 (s, 3H), 3.06 (s, 1H), 3.03 (d, 1H, J=2.4 Hz), 2.56 (s, 2H), 1.22 (t, 3H, J=7.25).

Workup

  1. temperaturecooled to room temperature
  2. washthe solution was washed with water, sodium carbonate, and water
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-9d83324d97d345c5ab05de041dadf7ec
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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