Hydrochloric Acid → HCID 91613659, compound

HRID 379099Notes

Reaction equation

HRID 379099 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2.O[CH2:19][P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23].Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:17])[C:14]([O:16][CH2:19][P:20]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:27])=[O:15])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 76513Diethyl phosphonomethanolHCID 156391NaproxenHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 91613659HCID 91613659, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (4.8 g, 20.85 mmol), diethyl (hydroxymethyl)phosphonate (3.76 g, 22.36 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (4.29 g, 22.38 mmol) and 4-(dimethylamino)pyridine (catalytic amount) in CH2Cl2 (125 mL) were stirred at room temperature for 2 hours. The reaction was taken up with 0.3 N HCl (150 mL) and extracted with CH2Cl2 (3×50 mL). The combined extracts were washed with water (2×50 mL), dried over Na2SO4, and evaporated under reduced pressure. The product was purified by silica gel column chromatography eluting with 2:1 EtOAc:Hex to obtained the title compound as a viscous oil, 5.23 g (66%). 1H NMR (300 MHz, CDCl3) δ 7.70-7.68 (mult, 3H), 7.43-7.37 (mult, 1H), 7.15-7.09 (mult, 2H), 4.38 (d, JH-P=8.6 Hz, 2H), 4.05-3.85 (mult, 5H), 3.95 (s, 3H), 1.60 (d, J=7.2 Hz, 3H), 1.25-1.1 (mult, 6H); 13C NMR (75 MHz, CDCl3) δ 173.5 (d, JC-P=7.9 Hz), 157.7, 134.9, 133.7, 129.1, 128.8, 127.1, 126.1, 119.0, 105.5, 62.71, 62.62, 62.61, 62.52, 57.1 (d, JC-P=167.0 Hz), 55.2, 45.1, 18.3, 16.20, 16.18, 16.12, 16.11; mass spectrum (API-TIS) m/z 381 (M+H). Anal Calcd for C19H25O6P: C, 60.0; H, 6.62. Found: C, 59.83; H, 6.41.

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. washThe combined extracts were washed with water (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe product was purified by silica gel column chromatography
  6. washeluting with 2:1 EtOAc

Sources & evidence

ORD record
ord-572d1313345646d9ae7cc986bcca6b66
Source dataset
uspto-grants-2001_10
Patent number
US06297260B1

Reaction notes

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