HCID 178476815, compound → HCID 178511511, compound

HRID 1062532Notes

Reaction equation

HRID 1062532 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][PH:18](=[O:22])[O:19]CC)[CH2:10]1)=O)(C)(C)C>Cl>[NH2:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][PH:18](=[O:19])[OH:22])[CH2:10]1

Participants

3

Reactant 1

HCID 178476815HCID 178476815, compound

Product 1

HCID 178511511HCID 178511511, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (±)-cis-ethyl [3-(t-butyloxycarbonyl)aminocyclopentanyl]butylphosphinate (14) (1.07 g, 3.21 mmol) was dissolved in aqueous HCl (6 M, 40 cm3) and the solution heated at reflux for 30 hours. After cooling, the solution was evaporated to dryness under reduced pressure. The residue was dissolved in water (10 cm3) and applied to an ion exchange column (Dowex 50, H+). The column was eluted with water until the eluate was colourless and the pH 7. On further elution with aqueous pyridine (1 M), ninhydrin positive fractions were collected and the solvent removed in vacuo. Residual traces of pyridine were removed by repeatedly redissolving the compound in water (20 cm3) and re-evaporating (3 times). Recrystallisation from ethanol/acetone followed by drying gave the desired title compound (15) as an off white solid (450 mg, 68%, m.p. (dec.) 180-183° C.): 1H-NMR (300 MHz, D2O) δH 0.68 (3H, 2×d, J=6.9 and 7.2 Hz, PCH2CH2CH2CH3),1.02-2.43 (13H, m, C(1)—H, C(2)—H, C(2)—H′, C(4)—H, C(4)—H′, C(5)—H and C(5)—H′, PCH2CH2CH2CH3, PCH2CH2CH2CH3,PCH2CH2CH2CH3),3.56 (1H, m, C(3)—H); 13C-NMR (75 MHz, D2O) δC 13.46 (s, PCH2CH2CH2CH3), 24.11 and 24.31 (d, 3JPC=15.17 Hz, PCH2CH2CH2CH3), 24.31 (s, C(5)), 24.53 and 24.56 (d, 2JPC=2.87 Hz, PCH2CH2CH2CH3), 27.96 and 29.17 (d, JPC=91.32 Hz, PCH2CH2CH2CH3),31.12 and 31.20 (d, 2JPC=6.3 Hz, C(2)), 31.95 (s, C(4)), 36.14 and 37.38 (d, JPC=93.33 Hz, C(1)), 52.97 and 52.88 (d, 3JPC=7.15 Hz, C(3)); 31P-NMR (121MHz, D2O) δP 50.74; MS (ESI) m/z 205.9 (37%) (MH+), 411.3 (100), 484.3 (14), 102.4 (12).

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 30 hours
  3. temperatureAfter cooling
  4. customthe solution was evaporated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in water (10 cm3)
  6. washThe column was eluted with water until the eluate
  7. washOn further elution with aqueous pyridine (1 M), ninhydrin positive fractions
  8. customwere collected
  9. customthe solvent removed in vacuo
  10. customwere removed
  11. dissolutionby repeatedly redissolving the compound in water (20 cm3)
  12. customre-evaporating (3 times)
  13. customRecrystallisation from ethanol/acetone
  14. customby drying

Sources & evidence

ORD record
ord-c7414ae8f103425baa2d0f77161f3afa
Source dataset
uspto-grants-2005_11
Patent number
US06962907B2

Reaction notes

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