3-Fluoro-4-nitroanisole → HCID 44322538, compound

HRID 2379456Notes

Reaction equation

HRID 2379456 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.[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[C:23](F)[CH:24]=1>[OH-].[Na+].C(O)C>[NH2:8][C@@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:21]1[CH:20]=[C:19]([O:18][CH3:17])[CH:24]=[CH:23][C:22]=1[N+:26]([O-:28])=[O:27])[C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 5656543-Fluoro-4-nitroanisoleHCID 7018784(2S)-5-amino-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

Product 1

HCID 44322538HCID 44322538, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 696 mg (3.0 mmol) of Nα -BOC-L-ornithine and 513 mg (3 mmol) of 5-methoxy-2-nitrofluorobenzene in 3 mL of 1N NaOH and 3 mL of ethanol were heated at reflux for 20 hours, then concentrated in vacuo to a yellow oil. The oil was dissolved in 21 mL of 4N HCl in 33% acetic acid and stirred for 12 hours, then suspended in 50 mL of water and washed with 30 mL of dichloromethane and concentrated in vacuo to give a yellow powder. This was recrystallized twice from acetic acid/water to afford the title product as yellow crystals. mp 245°-246°; MS M/Z (DCl/NH3) 284 [M+H]; 1H NMR (300 MHz, D2O/NaOD) δ: 8:1.45 (m, 4H), 2.81 (m, 2H), 3.10 (d, J=1 Hz, 4.2H), 3.52 (d, J=3 Hz, 5.7H), 5.52 (d, J=1 Hz, 3.0H), 5.69 (m, 1H), 7.33 (dd, J=1, 8.4 Hz, 5.7H); 13C NMR (75.5 MHz, D2O/NaOD) δ: 185.47, 168.65, 150.74, 131.00, 127.20, 108.64, 96.78, 58.48, 45.27, 35.37, 27.37; Analysis calc'd for C12H17N3O5.0.2 H2O: C, 50.24; H, 6.11; N, 14.65; found: C, 50.09; H, 6.03; N, 14.60.

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationconcentrated in vacuo to a yellow oil
  3. dissolutionThe oil was dissolved in 21 mL of 4N HCl in 33% acetic acid
  4. washwashed with 30 mL of dichloromethane
  5. concentrationconcentrated in vacuo
  6. customto give a yellow powder
  7. customThis was recrystallized twice from acetic acid/water

Sources & evidence

ORD record
ord-82f11a5809134bc3a2c171ea476e358b
Source dataset
uspto-grants-1994_11
Patent number
US05362747

Reaction notes

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