Methanol → HCID 66868945, compound

HRID 2281845Notes

Reaction equation

HRID 2281845 reaction equation
[NH2:1][C@@:2]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH2:6][O:5][CH2:4][C@H:3]1[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:22]O>>[NH2:1][C@@:2]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH2:6][O:5][CH2:4][C@H:3]1[C:7]([O:9][CH3:22])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 69937863HCID 69937863, compound

Product 1

HCID 66868945HCID 66868945, compound

Conditions

Temperature
70 °C

Procedure

(±)-(3S*,4S*)-4-Amino-4-(2-fluorophenyl)tetrahydrofuran-3-carboxylic acid (0.22 g) was transferred into the reaction vessel. Methanol (15 mL) was transferred into the reaction vessel. Sulphuric acid (1 mL) was transferred into the reaction vessel. The reaction was stirred at 70° C. for 8 h. The reaction mixture was concentrated under reduced pressure. Saturated sodium bicarbonate (40 mL) was then added followed by an extraction with DCM (3×40 mL). The combined organic phases were dried over MgSO4, filtered and concentrated. The crude product was purified by preparative HPLC (Method B) to give the title compound (120 mg). 1H NMR (400 MHz, CDCl3) δ ppm 3.73 (s, 3H) 3.78 (t, J=8.21 Hz, 1H) 4.02 (dd, J=8.91, 2.97 Hz, 1H) 4.15 (d, J=8.97 Hz, 1H) 4.22 (t, J=8.72 Hz, 1H) 4.36-4.44 (m, 1H) 7.09 (ddd, J=12.41, 8.12, 1.20 Hz, 1H) 7.18 (td, J=7.64, 1.14 Hz, 1H) 7.29-7.35 (m, 1H) 7.63 (td, J=8.05, 1.45 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionSaturated sodium bicarbonate (40 mL) was then added
  3. extractionfollowed by an extraction with DCM (3×40 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative HPLC (Method B)

Sources & evidence

ORD record
ord-c56041aa55d94d44b163b1d822f68e69
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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