Acetic Acid → HCID 72370696, compound

HRID 525777Notes

Reaction equation

HRID 525777 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH:13]([OH:18])[CH2:14][C:15](O)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.O(C(C)C)C(C)C>C1COCC1.CO>[OH:18][CH:13]([CH2:14][CH2:15][OH:16])[CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7914Diisopropyl EtherHCID 111185764-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoic acid

Product 1

HCID 72370696HCID 72370696, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 M BH3.THF complex (80 mL, 80 mmol) was added dropwise over 30 min to a solution of 4-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoic acid (prepared as described in Tetrahedron (1994), 50(47), 13347-68, 13.5 g, 53.3 mmol) in THF (53 mL) at 0° C. and the RM was stirred at RT overnight. 10% acetic acid in MeOH (250 mL) was added and the mixture was stirred at RT overnight. The solvent was evaporated off under reduced pressure and the residue was dissolved in EtOAc, washed with aq. sat. NaHCO3 solution and brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give a residue was treated with iPr2O, filtered and dried to afford the title compound as a white solid. UPLC-MS (Condition 8) tR=0.61 min, m/z=240 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29-1.45 (m, 1H) 1.48-1.61 (m, 1H) 2.98 (t, J=5.56 Hz, 2H) 3.49 (dt, J=11.62, 5.56 Hz, 2H) 3.54-3.65 (m, 1H) 4.35 (t, J=5.01 Hz, 1H) 4.58 (d, J=5.26 Hz, 1H) 5.02 (s, 2H) 7.16 (t, J=5.62 Hz, 1H) 7.26-7.44 (m, 5H).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customThe solvent was evaporated off under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with aq. sat. NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated off under reduced pressure
  7. customto give a residue
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-506944a1fe1e41809df9979618013e59
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

Loading…