Ethanol → HCID 10378286, compound

HRID 2379455Notes

Reaction equation

HRID 2379455 reaction equation
C([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH2:11][CH2:12][NH2:13])(OC(C)(C)C)=O.F[C:18]1[CH:19]=[C:20]([CH3:27])[CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25].C(O)C.[OH-].[Na+]>Cl.C(O)(=O)C.O>[NH2:8][C@@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:18]1[CH:19]=[C:20]([CH3:27])[CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:14]([OH:16])=[O:15]

Participants

8

Reactant 4

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-2×HCID 7018784(2S)-5-amino-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

Product 1

HCID 10378286HCID 10378286, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 474 mg (2 mmol) of Noc-BOC-L-ornithine (supplier BAChem) and 314 mg (2 mmol) of 3-fluoro-4-nitrotoluene (Aldrich Chemical Co.)in 2 mL of ethanol and 2 mL of 1N NaOH was heated at reflux for 12 hours. Another 2 mmol each of NaOH and 3-fluoro-4-nitrotoluene was added and the reaction was continued another two hours. The solution was poured into 50 mL of water and extracted with dichloromethane (2×80 mL). The organic phase was dried and concentrated to give a solid residue, which was stirred in 20 mL of 4N HCl in 33% acetic acid for four hours, filtered and concentrated to leave a yellow solid, which was recrystallized from ethanol/water to afford 296 mg (56% yield) of the title product as an amorphous orange powder. mp 263°-264° (decomp.); MS M/Z 268 [M+H], 285 [M+NH4 ]; 1H NMR (300 MHz, D2O/NaOD) δ: 1.64 (m, 4H)2.18 (s, 3H), 3.12 (m, 2H), 3.30 (t, J=4.5 Hz, 1H), 6.22 (d, J=8.1 Hz, 1H), 6.43 (s, 1H), 7.58 (d, J=8.1 Hz, 1H); 13C NMR (75.5 MHz, D2O/NaOD) δ: 185.88, 158.28, 148.71, 130.81,128.71,120.22, 116.11, 58.73, 45.24, 35.40, 27.73, 24.24; Analysis calc'd for C12H17N3O4.0.4 HCl: C, 50.81; H, 6.25; N, 14.81; found: C, 50.79; H, 6.27; N, 14.73.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. extractionextracted with dichloromethane (2×80 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customto give a solid residue, which
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto leave a yellow solid, which
  10. customwas recrystallized from ethanol/water

Sources & evidence

ORD record
ord-8568c42fe1ad41e49e57c01802722e7a
Source dataset
uspto-grants-1994_11
Patent number
US05362747

Reaction notes

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