Hydrochloric Acid → HCID 11294884, compound

HRID 2252444Notes

Reaction equation

HRID 2252444 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:43])[CH2:9][CH2:10][C@@H:11]2[C@@H:14]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([B:27]5[O:31]C(C)(C)C(C)(C)[O:28]5)[CH:22]=4)=[CH:17][CH:16]=3)[N:13]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:12]2=[O:42])=[CH:4][CH:3]=1.O.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:43])[CH2:9][CH2:10][C@H:11]2[C:12](=[O:42])[N:13]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C@@H:14]2[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([B:27]([OH:28])[OH:31])[CH:22]=3)=[CH:17][CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 69117633HCID 69117633, compound

Product 1

HCID 11294884HCID 11294884, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3R,4S)-3-[(3S)-3-(4-Fluorophenyl)-3-hydroxypropyl]-1-phenyl-4-[3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-yl]azetidin-2-one (0.020 g, 0.034 mmol) was dissolved in ethanol (3 mL) and water (1 mL) at room temperature. Solid sodium carbonate (0.10 g, 1.2 mmol) was added and the mixture was rapidly stirred 2 h at room temperature. The solution was poured into 0.5 N hydrochloric acid (4 mL) and extracted with ethyl acetate. The organic phase was washed successively with water (2×) and brine, then dried over sodium sulfate, filtered and the solvent was removed by rotary evaporation under reduced pressure. The residue was purified by reverse-phase HPLC (Polaris C18-A 10 μ 250×21.2 mm column, 40% to 75% acetonitrile-0.1% trifluoroacetic acid in water) to afford (4′-{(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-3-yl)boronic acid as a white powder (0.012 g, 70%); 1H NMR (300 MHz, CD3OD) δ 7.83 (br s, 1H), 7.0-7.7 (m, 16H), 4.92 (d, J=2.7 Hz, 1H), 4.63 (t, J=6.2 Hz, 1H), 3.1-3.2 (m, 1H), 1.8-2.1 (m, 4H) ppm; MS [M+HCO2−]− 540.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed successively with water (2×) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed by rotary evaporation under reduced pressure
  7. customThe residue was purified by reverse-phase HPLC (Polaris C18-A 10 μ 250×21.2 mm column, 40% to 75% acetonitrile-0.1% trifluoroacetic acid in water)

Sources & evidence

ORD record
ord-c2691aaff3b74d00a017fbbdd4316fa1
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

Loading…