Methanol → HCID 14730655, compound

HRID 2051558Notes

Reaction equation

HRID 2051558 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([NH:10][C@H:11]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:9])=[CH:6][C:5]=1[F:26])([O-])=O.CO>C(O)C.[Pd]>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([C:8]([NH:10][C@H:11]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:9])=[CH:6][C:5]=1[F:26]

Participants

5

Reactant 2

HCID 887MethanolHCID 14730628HCID 14730628, compound

Product 1

HCID 14730655HCID 14730655, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of diethyl N-(4-nitro-3-fluorobenzoyl)-(L)-glutamate (5.3 g, 14 mmoles) in 95% ethanol (150 mL) was mixed with 10% palladium on carbon (0.4 g) and placed on a Parr apparatus. The mixture was shaken under hydrogen atmosphere for 1.5 hours. The reaction mixture was filtered, spin evaporated, and dried to give a cream solid; yield, 4.7 g (98%); mp 92°-97° C.; 1H-NMR (CDCl3) δ 1.22 and 1.29 (2t overlapped, 6H), 1.6 (br s, 2H), 2.1-2.5 (m, 4H), 4.10 and 4.22 (2q overlapped, 4H), 4.74 (m, 1H), 6.75 (t, 1H), 6.84 (d, 1H), 7.4-7.5 (m, 2H); uv (MeOH) 281 nm max (12000), 236 min (1480), 210 sh (10600); mass spec (CI) m/e 341 (100%), 138 (64).

Workup

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

Sources & evidence

ORD record
ord-a1a324daa132444ba5831b7f501ead3c
Source dataset
uspto-grants-1991_05
Patent number
US05019577

Reaction notes

Loading…