Water → HCID 86742660, compound

HRID 2291542Notes

Reaction equation

HRID 2291542 reaction equation
[N:1]([CH:4]1[C@@:16]2([CH2:17][CH2:18][CH3:19])[C:11](=[CH:12][C:13](=[O:20])[CH2:14][CH2:15]2)[C:10]2[C:5]1=[CH:6][C:7]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:8]([Cl:22])[C:9]=2[Cl:21])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[ClH:21].[NH2:1][CH:4]1[C@@:16]2([CH2:17][CH2:18][CH3:19])[C:11](=[CH:12][C:13](=[O:20])[CH2:14][CH2:15]2)[C:10]2[C:5]1=[CH:6][C:7]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:8]([Cl:22])[C:9]=2[Cl:21]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57027529HCID 57027529, compound

Product 1

HCID 86742660HCID 86742660, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl [(9-azido-5,6-dichloro-3-oxo-9a(R)-propyl-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]acetate (2.229 g, 0.00517 mole) and triphenylphosphine (1.493 g, 0.00569 mole) in tetrahydrofuran (30 ml) was refluxed with stirring for 4 hours. Then, water (0.4 ml) was added and refluxing was continued for another 16 hours. After cooling and evaporating the solvents in vacuo, the residue was dissolved in ether, dried over sodium sulfate, filtered and the filtrate acidified with ethanolic hydrogen chloride. The solid that separated was removed by filtration, washed with hot ethanol and dried. The ethyl [(9-amino-5,6-dichloro-3-oxo-9a(R)-propyl-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]acetate hydrochloride weighed 940 mg; m.p. 261° C.(d).

Workup

  1. temperaturerefluxing
  2. waitwas continued for another 16 hours
  3. temperatureAfter cooling
  4. customevaporating the solvents in vacuo
  5. dissolutionthe residue was dissolved in ether
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solid that separated
  9. customwas removed by filtration
  10. washwashed with hot ethanol
  11. customdried

Sources & evidence

ORD record
ord-ec0c350d3a5e459b8cc5268b7b8718d9
Source dataset
uspto-grants-1989_01
Patent number
US04797391

Reaction notes

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