HCID 89559790, compound → HCID 89560151, compound

HRID 1747226Notes

Reaction equation

HRID 1747226 reaction equation
C([O:3][C:4](=O)[C:5]([NH2:15])([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=1)C>C1COCC1>[NH2:15][C:5]([CH3:14])([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=1)[CH2:4][OH:3]

Participants

3

Reactant 1

HCID 89559790HCID 89559790, compound

Product 1

HCID 89560151HCID 89560151, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

BH3.THF Complex 1 M soln. in THF (9 mL, 9 mmol) was added dropwise to a 0° C. solution of rac-2-amino-3-(3-iodo-phenyl)-2-methyl-propionic acid ethyl ester H-5 (1.2 g, 3.6 mol) in THF (10 mL) under argon and the resulting mixture was stirred for 5 min at 0° C. before being warmed to RT and stirred overnight. The reaction mixture was cooled to 0° C. and quenched with MeOH before being evaporated in vacuo. The residue was partioned between 2M aq. HCl and TBME and stirred for 30 min. The phases were separated and the aqueous phase was re-extracted with TBME (2×) and the combined organic extracts were discarded. The aqueous layer was basified with 2M aq. NaOH and re-extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the title compound as a white solid. LC-MS D: tR=0.74 min; [M+H+MeCN]+=333.02.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with MeOH
  3. custombefore being evaporated in vacuo
  4. stirringstirred for 30 min
  5. customThe phases were separated
  6. extractionthe aqueous phase was re-extracted with TBME (2×)
  7. extractionre-extracted with DCM (3×)
  8. washThe combined DCM extracts were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-e8e7ca1715e4478d95377565647771b1
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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