Acetic Acid → HCID 57725383, compound

HRID 1091435Notes

Reaction equation

HRID 1091435 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH:7]([NH:10][C:11](=[O:20])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[NH2:19])[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:22](O)(=O)C>COC(OC)OC>[C:1]([O:5][C:6](=[O:21])[C@@H:7]([N:10]1[C:11](=[O:20])[C:12]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)[N:19]=[CH:22]1)[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 66593713HCID 66593713, compound

Product 1

HCID 57725383HCID 57725383, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

2-(2-amino-5-chloro-benzoylamino)-butyric acid-tert-butyl ester (2.82 g) was dissolved in trimethylorthoformate (50 ml). Acetic acid (10 ml) was added, and reaction mixture refluxed for 48 hours. After this time, the solvents were removed and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The aqueous layer was further extracted with ethyl acetate and the combined organic extracts washed with brine, dried (MgSO4) and concentrated under reduced pressure to give a yellow oil. This was purified by flash chromatography (20% EtOAc: Petroleum) to give the sub-title compound as an oil (1.23 g, 42% yield). 1H NMR (400 MHz, CDCl3) δ 8.25 (1H, s), 8.05 (1H, s), 7.7 (2H, m), 5.3 (1H, m), 2.3 (1H, m), 2.0 (1H, m), 1.5 (9H, s), 1.0 (3H, t) ppm.

Workup

  1. customreaction mixture
  2. temperaturerefluxed for 48 hours
  3. customAfter this time, the solvents were removed
  4. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  5. extractionThe aqueous layer was further extracted with ethyl acetate
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customto give a yellow oil
  10. customThis was purified by flash chromatography (20% EtOAc: Petroleum)

Sources & evidence

ORD record
ord-3cc630935930483d92e2ad72f70d0e5b
Source dataset
uspto-grants-2012_03
Patent number
US08129381B2

Reaction notes

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