Methanol → HCID 14986741, compound

HRID 2051560Notes

Reaction equation

HRID 2051560 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[N+:24]([O-])=O)[C:5]([NH:7][C@H:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:6].CO>C(O)C.[Pd]>[NH2:24][C:23]1[CH:22]=[CH:21][C:4]([C:5]([NH:7][C@H:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:6])=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 887MethanolHCID 14986740HCID 14986740, compound

Product 1

HCID 14986741HCID 14986741, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of diethyl N-(3-methyl-4-nitrobenzoyl)-(L)-glutamate (Cosulich, D. B. et al., J. Am. Chem. Soc., 1953, 75, 4675) (11.0 g, 30.0 mmoles) in 95% ethanol (250 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 2 hours. The reaction mixture was filtered, spin evaporated, and dried to give a beige solid; yield, 10.1 g (100%); mp 79°-82° C.; 1H-NMR (DMSO-d6) δ 1.15 and 1.16 (2t overlapped, 6H), 2.00 (m, 2H), 2.06 (s, 3H), 2.39 (t, 2H), 4.03 and 4.06 (2q overlapped, 4H), 4.33 (m, 1H), 5.40 (s, 2H), 6.56 (d, Jo=8 Hz, 1H), 7.47 (d, Jo=8 Hz, 1H), 7.50 (s, 1H), 8.16 (d, 1H); uv (MeOH) 284 nm max (17000), 241 min (3020); mass spec (CI) m/e 337 (44%), 134 (100).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customspin evaporated
  3. customdried
  4. customto give a beige solid
  5. customyield

Sources & evidence

ORD record
ord-528d067e92af4643b82e5ed81c233509
Source dataset
uspto-grants-1991_05
Patent number
US05019577

Reaction notes

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