Water → HCID 86587361, compound

HRID 2120334Notes

Reaction equation

HRID 2120334 reaction equation
[CH2:1]([O:3][CH:4]([O:6][C@@H:7]1[CH2:15][C@@H:10]2[O:11][CH:12]([OH:14])[CH2:13][C@@H:9]2[C@H:8]1[CH2:16][CH2:17][C@@H:18]([O:27][CH:28]([O:30][CH2:31][CH3:32])[CH3:29])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:5])[CH3:2].[OH2:33].C(O[CH2:38][CH3:39])(=O)C.[CH2:40](O)[C:41](N)(CO)[CH2:42]O>C1COCC1>[CH2:1]([O:3][CH:4]([O:6][C@@H:7]1[CH2:15][C@H:10]([OH:11])[C@@H:9]([C@@H:13]([CH2:40][CH2:41][CH:42]=[CH:38][CH3:39])[C:12]([OH:33])=[O:14])[CH:8]1[CH2:16][CH2:17][C@@H:18]([O:27][CH:28]([O:30][CH2:31][CH3:32])[CH3:29])[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6503Tris(hydroxymethyl)aminomethaneHCID 8857Ethyl AcetateHCID 57466765HCID 57466765, compound

Product 1

HCID 86587361HCID 86587361, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3aR,4R,5R,6aS)-5-(1-Ethoxyethoxy)-4-[(3R)-3-(1-ethoxyethoxy)-5-phenylpentyl]hexahydro-2H-cyclopenta[b]furan-2-ol (XI, EXAMPLE 7) is dissolved in dry THF (10 mL) and added to a mixture containing potassium 5-(triphenylphosphoranylidene)pentaonate (PREPARATION 1) solution at −10° to −5°. The resulting mixture is stirred for about 3 hours at less than −5°. Water (30 mL; 0°) is added over 10 minutes, then ethyl acetate (20 mL) and aqueous THAM solution (10 mL) is added. The phases are separated and the organic phase is washed with aqueous THAM solution (15%, 2×15 mL). The aqueous phases are combined and washed once with ethyl acetate (15 mL). MTBE (50 mL) is added to the combined aqueous phases. The mixture is acidified to pH=3 with aqueous phosphoric acid (40%). The organic phase is separated and concentrated under reduced pressure to 20 mL. Solids (5-diphenypphosphinopentanoic acid) crystallized. MTBE (50 mL) is added and the slurry concentrated under reduced pressure to a volume of 20 mL. The solid is filtered and washed with MTBE (100 mL). The filtrate is concentrated under reduced pressure to give the title compound.

Workup

  1. additionadded to a mixture
  2. customThe phases are separated
  3. washthe organic phase is washed with aqueous THAM solution (15%, 2×15 mL)
  4. washwashed once with ethyl acetate (15 mL)
  5. additionMTBE (50 mL) is added to the combined aqueous phases
  6. customThe organic phase is separated
  7. concentrationconcentrated under reduced pressure to 20 mL
  8. customSolids (5-diphenypphosphinopentanoic acid) crystallized
  9. additionMTBE (50 mL) is added
  10. concentrationthe slurry concentrated under reduced pressure to a volume of 20 mL
  11. filtrationThe solid is filtered
  12. washwashed with MTBE (100 mL)
  13. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d21d0cbce1d545148cbc351610374525
Source dataset
uspto-grants-2004_02
Patent number
US06689901B2

Reaction notes

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