Sodium Bicarbonate → (S)-3-(3-Bromo-5-tert-butyl-phenyl)-3-(2-tert-butoxycarbonylamino-acetylamino)-propionic acid ethyl ester

HRID 1526767Notes

Reaction equation

HRID 1526767 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:24])[CH2:6][C@H:7]([NH:19][C:20](=[O:23])[CH2:21][NH2:22])[C:8]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=[C:10]([Br:18])[CH:9]=1)[CH3:3].[C:25]([O-:28])(O)=[O:26].[Na+]>O1CCOCC1>[CH2:2]([O:4][C:5](=[O:24])[CH2:6][C@@H:7]([C:8]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=[C:10]([Br:18])[CH:9]=1)[NH:19][C:20](=[O:23])[CH2:21][NH:22][C:25]([O:28][C:8]([CH3:13])([CH3:9])[CH3:7])=[O:26])[CH3:3]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86709935(S)-3-(2-Amino-acetylamino)-3-(3-bromo-5-tert-butyl-phenyl)-propionic acid ethyl ester hydrochloride salt

Product 1

HCID 86709934(S)-3-(3-Bromo-5-tert-butyl-phenyl)-3-(2-tert-butoxycarbonylamino-acetylamino)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product from example H (2 gm, 5.204 mmol) in 1,4-Dioxane (20 ml) was added saturated aq. NaHCO3 solution (2.5 ml) and stirred for 5 min at RT. Boc-anhydride (1.36 ml, 6.245 mmol) was then added to it at 0 C and the reaction mixture was allowed to stir at room temperature for 2 hrs. Reaction mixture was concentrated, dissolved in EtOAc (60 ml) and washed with water (60 ml), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude which was purified by silica gel (100-200 mesh) column chromatography eluting with 10% EtOAc to afford the desired compound (1.7 g) as a colorless liquid.

Workup

  1. stirringto stir at room temperature for 2 hrs
  2. customReaction mixture
  3. concentrationwas concentrated
  4. dissolutiondissolved in EtOAc (60 ml)
  5. washwashed with water (60 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto obtain the crude which
  10. customwas purified by silica gel (100-200 mesh) column chromatography
  11. washeluting with 10% EtOAc

Sources & evidence

ORD record
ord-0e59eadc361f413aaad0936146965d6a
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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