Methanol → HCID 14986745, compound

HRID 2051564Notes

Reaction equation

HRID 2051564 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[N+:25]([O-])=O)[C:6]([NH:8][C@H:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:7].CO>C(O)C.[Pd]>[NH2:25][C:24]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C@H:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 887MethanolHCID 14986744HCID 14986744, compound

Product 1

HCID 14986745HCID 14986745, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of diethyl N-(3-methoxy-4-nitrobenzoyl)-(L)-glutamate (11.0 g, 28.8 mmoles) in 95% ethanol (200 mL) was mixed with 10% palladium on carbon (0.8 g) and placed on a Parr apparatus. The mixture was shaken under hydrogen atmosphere for 1 hour. The reaction mixture was filtered, spin evaporated, and dried to give a clear viscous oil which on long-standing hardened to a white wax; yield, 9.95 g (99%); 1H-NMR (DMSO-d6) δ 1.15 and 1.17 (2t overlapped, 6H), 1.8-2.2 (m, 2H), 2.40 (t, 2H), 3.79 (s, 3H), 4.0-4.2 (2 q overlapped, 4H), 4.36 (m, 1H), 5.29 (br s, 2H), 6.60 (d, Jo =8 Hz, 1H), 7.3-7.4 (m, 2H), 8.25 (d, 1H); uv (MeOH) 301 nm max (17800), 280 sh (15700), 266 min (12600), 263 max (13200), 256 sh (12500), 245 min (8630), 204 max (40900); mass spec (CI) m/e 353 (56%), 150 (100).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customspin evaporated
  3. customdried
  4. customto give a clear viscous oil which
  5. customyield

Sources & evidence

ORD record
ord-e6cf46d73fdb4d6dabf21bbdee5e5fc3
Source dataset
uspto-grants-1991_05
Patent number
US05019577

Reaction notes

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