di-tert-butyl N-(4-nitro-2-fluorobenzoyl)-(L)-glutamate → 4-Amino-2-fiuorobenzoylglutamic acid di-t-butyl ester

HRID 2051557

Reaction equation

HRID 2051557 reaction equation
[C:1]([O:5][C:6](=[O:30])[C@H:7]([CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[NH:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=1[F:19])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][C@H:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:30])[CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])=[C:11]([F:19])[CH:12]=1

Participants

4

Reactant 1

HCID 10071104di-tert-butyl N-(4-nitro-2-fluorobenzoyl)-(L)-glutamate

Product 1

HCID 100693194-Amino-2-fiuorobenzoylglutamic acid di-t-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of di-tert-butyl-N (4-nitro-2-fluorobenzoyl)-(L)-glutamate (3.6 g, 8.4 mmoles) in 95% ethanol (100 mL) was mixed with 10% palladium on carbon (0.25 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 white solid, di-tert-butyl N-(4-amino-2-fluorobenzoyl)-(L)-glutamate yield, 3.0 g (91%); mp 91°-95° C.; 1H-NMR (CDCl3) δ 1.41 (s, 9H), 1.48 (s, 9H), 2.0-2.4 (m, 4H), 2.8 (br s, 2H), 4.71 (m, 1H), 6.34 (d, 1H), 6.48 (d, 1H), 7.17 (q, 1H), 7.86 (t, 1H); uv (MeOH) 280 nm max (16800), 238 min (2760), 212 sh (12100); mass spec (CI) m/e 397 (21 %), 341 (13), 285 (100).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customspin evaporated
  3. customdried

Sources & evidence

ORD record
ord-5cf6e6fc0d2e401d92f3183f4035c224
Source dataset
uspto-grants-1991_05
Patent number
US05019577

Linked notes

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