Tetrahydrofuran → HCID 10227850, compound

HRID 1358135Notes

Reaction equation

HRID 1358135 reaction equation
COC1C=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]1[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][C:6]=1[CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH:21]=O)[CH:14]=1)[O:8]2.[Br-].[CH3:33][O:34][CH2:35][CH2:36][PH3+].[OH-].[Na+].C1[CH2:44][O:43][CH2:42][CH2:41]1>CCOC(C)=O.[Cl-].[Na+].O>[CH3:33][O:34][C:35]1[CH:36]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]1[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])=[CH:23][C:6]=1[CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH2:21][CH2:41][CH2:42][O:43][CH3:44])[CH:14]=1)[O:8]2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18189190HCID 18189190, compoundHCID 87644280HCID 87644280, compound

Product 1

HCID 10227850HCID 10227850, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of Example 94A (0.05 g, 0.114 mmol), methoxyethylphosphonium bromide (0.068 g, 0.171 mmol) and aqueous sodium hydroxide (1 mL, 6.0M) in THF (1 mL) was stirred for 16 hours, and then diluted with EtOAc (10 mL) and brine (25 mL). The layers were separated and the organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The residue and 10% Pd on carbon (0.005 g) in anhydrous THF (2 mL) were shaken under hydrogen gas (balloon) for 6 hours. The mixture was filtered through diatomaceous earth (Celite®), washing the filtrant with dry TUF (2×20 mL). The combined organics were concentrated under reduced pressure and purified by HPLC using 0.1% TFA and MeCN to provide the titled compound (1H NMR (300 MHz, DMSO-d6) δ 9.84 (s, 1H), 8.33 (d, J=9 Hz, 1H), 7.26-7.22 (m, 2H), 7.15 (t, J=8 Hz, 1H), 6.92-6.80 (m, 4H), 6.73 (d, J=8 Hz, 1H), 6.65 (d, J=9 Hz, 1H), 6.18 (s, 1H), 3.89 (t, J=6 Hz, 2H), 3.88 (s, 3H), 3.46-3.43 (m, 2H), 3.21 (s, 3H), 3.00 (s, 3H), 1.71-1.57 (m, 4H); MS (ESI, −Q1MS) m/e 508 (M−H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe mixture was filtered through diatomaceous earth (Celite®)
  6. washwashing the filtrant
  7. customwith dry TUF (2×20 mL)
  8. concentrationThe combined organics were concentrated under reduced pressure
  9. custompurified by HPLC

Sources & evidence

ORD record
ord-8874d06296c44dc08425c9deb94c8fc5
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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