Tetrahydrofuran → HCID 91938061, compound

HRID 1054320Notes

Reaction equation

HRID 1054320 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([C:11]([O:13]CC)=[O:12])=[CH:8][C:7](/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][C:5]=2[N:4]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)[N:3]=1.[OH-].[K+].C1COCC1>CC(O)C.O>[CH3:1][C:2]1[C:10]2[C:9]([C:11]([OH:13])=[O:12])=[CH:8][C:7](/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][C:5]=2[N:4]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:29][CH:30]=2)[N:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 118423379HCID 118423379, compound

Product 1

HCID 91938061HCID 91938061, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of ester 52 (56 mg, 0.11 mmol) and KOH (19 mg, 0.34 mmol) in iPrOH:THF (2 mL/1 mL) was refluxed at 87° C. for 2 h. Reaction mixture was diluted with water (10 mL) and washed with EtOAc (10 mL×2). Aqueous layer was acidified with 1N HCl and extracted with EtOAc (10 mL×2). Combined organic extracts were washed with brine, dried (Na2SO4) and filtered. The solvent was removed under reduced pressure to give the title compound (45 mg, 94%) as a yellow solid. 88% pure by HPLC. 1H NMR (500 MHz, DMSO-d6) δ 13.86 (s, 1H), 7.87 (d, J=16.2 Hz, 1H), 7.81 (s, 1H), 7.74 (d, J=7.8 Hz, 2H), 7.52 (d, J=16.2 Hz, 1H), 7.42 (t, J=7.5 Hz, 2H), 7.37-7.29 (m, 5H), 7.09 (t, J=7.4 Hz, 1H), 6.98-6.92 (m, 4H), 5.64 (s, 2H), 2.58 (s, 3H). 13C NMR (125 MHz, DMSO-d6) δ 167.16, 156.97, 156.47, 155.22, 152.20, 140.74, 136.47, 135.39, 134.92, 133.00, 130.46, 129.90, 129.30, 128.04, 127.87, 123.90, 119.11, 119.02, 116.60, 110.13, 49.41, 16.02. ESI MS: m/z 462.0 (M+H)+.

Workup

  1. customReaction mixture
  2. washwashed with EtOAc (10 mL×2)
  3. extractionextracted with EtOAc (10 mL×2)
  4. washCombined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-24f97f651a7f4291bccc8add3ea14d62
Source dataset
uspto-grants-2016_07
Patent number
US09394303B2

Reaction notes

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