Tetrahydrofuran → HCID 178448635, compound

HRID 2042713Notes

Reaction equation

HRID 2042713 reaction equation
[CH2:1]([N:5]1[C:13]2[C:12]([OH:14])=[N:11][CH:10]=[N:9][C:8]=2[S:7]/[C:6]/1=[N:15]\[C:16](=[O:28])[C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1F)[CH2:2][CH2:3][CH3:4].[CH2:29]([OH:33])[C@@H:30]([OH:32])[CH3:31].CC(C)([O-])C.[K+].C1COCC1>C(O)(=O)C>[CH2:1]([N:5]1[C:13]2[C:12]([OH:14])=[N:11][CH:10]=[N:9][C:8]=2[S:7]/[C:6]/1=[N:15]\[C:16](=[O:28])[C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1[O:33][CH2:29][C@@H:30]([OH:32])[CH3:31])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 439846(S)-propane-1,2-diolHCID 23665647Potassium tert-butoxideHCID 178448627HCID 178448627, compound

Product 1

HCID 178448635HCID 178448635, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of Example 1B (65 mg, 0.16 mmol), (S)-propane-1,2-diol (28 mg, 0.36 mmol) and 1N solution of potassium tert-butoxide in THF (0.33 mL, 0.33 mmol) was heated at 45° C. for 18 hours. The mixture was acidified to pH 5 with acetic acid then concentrated under reduced pressure. The residue was stirred with saturated aqueous NaHCO3, extracted with EtOAc, concentrated, and the residue was purified by chromatography (EtOAc-EtOH 19:1) to afford 50 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.90-0.96 (m, 3H) 1.19 (d, J=5.76 Hz, 3H) 1.30-1.41 (m, 2H) 1.77-1.86 (m, 2H) 3.93-4.08 (m, 3H) 4.66-4.76 (m, 2H) 4.87 (d, J=4.07 Hz, 1H) 7.36 (d, J=8.82 Hz, 1H) 7.82 (dd, J=8.82, 2.03 Hz, 1H) 8.22 (s, 2H) 13.12 (s, 1H). MS (ESI) m/z 471 (M+H)+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography (EtOAc-EtOH 19:1)

Sources & evidence

ORD record
ord-5f972ce56a5a4d13bff3ad531266d28a
Source dataset
uspto-grants-2013_11
Patent number
US08586596B2

Reaction notes

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