Triethylamine → HCID 10071104, compound

HRID 2051556

Reaction equation

HRID 2051556 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[C:15]([O:19][C:20](=[O:32])[C@H:21]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[NH2:22])([CH3:18])([CH3:17])[CH3:16].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.CO>[N+:11]([C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH:22][C@H:21]([C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:32])[CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])=[O:6])=[C:2]([F:1])[CH:10]=1)([O-:13])=[O:12]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 208636Di-tert-butyl glutamate hydrochlorideHCID 3026792-Fluoro-4-nitrobenzoic acid

Product 1

HCID 10071104HCID 10071104, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-fluoro-4-nitrobenzoic acid (6.26 g, 33.8 mmoles), (L)-glutamate di-tert-butyl ester hydrochloride (10.0 g, 33.8 mmoles), and 1-hydroxybenzotriazole (4.57 g, 33.8 mmoles) in dry dimethylformamide (150 mL) was stirred under nitrogen while triethylamine (3.42 g, 4.71 mL, 33.8 mmoles) was added in one portion. After 15 minutes, 1.3-dicyclohexylcarbodiimide (7.67 g, 37.2 mmoles) was added in portions during 1 minute. The reaction mixture was filtered after 20 hours and the solids rinsed with dichloromethane (1×50 mL). The filtrate was spin evaporated to an amber residue that was partitioned between dichloromethane and saturated bicarbonate solution (200 mL each). The organic phase was washed successively with saturated bicarbonate, 5% citric acid, and brine (1×200 mL each). The organic phase was then dried (MgSO4), filtered, spin evaporated, and dried (high vacuum) to an oily yellow solid (11.9 g, 83%) that showed a major spot on tlc (silica, 2:1 hexane/ethyl acetate, Rf =0.5). The product was purified by the flash chromatography technique to give a light green gum; yield, 9.7 g (67%); 1H-NMR (CDCl3) δ 1.42 (s, 9H), 1.50 (s, 9H), 2.02-2.41 (m, 4H), 4.72 (m, 1H), 7.44 (br t, 1H), 8.0-8.3 (m, 3H); uv (MeOH) 260 nm max (11000), 225 min (4710), 215 sh (7680); mass spec (CI) m/e 427 (24%), 371 (20), 315 (100).

Workup

  1. additionwas added in one portion
  2. filtrationThe reaction mixture was filtered after 20 hours
  3. washthe solids rinsed with dichloromethane (1×50 mL)
  4. customevaporated to an amber residue that
  5. customwas partitioned between dichloromethane and saturated bicarbonate solution (200 mL each)
  6. washThe organic phase was washed successively with saturated bicarbonate, 5% citric acid, and brine (1×200 mL each)
  7. dry with materialThe organic phase was then dried (MgSO4)
  8. filtrationfiltered
  9. customspin evaporated
  10. dry with materialdried (high vacuum) to an oily yellow solid (11.9 g, 83%) that
  11. customThe product was purified by the flash chromatography technique
  12. customto give a light green gum
  13. customyield

Sources & evidence

ORD record
ord-814f335b1faf48bf9ce10d50f93957d0
Source dataset
uspto-grants-1991_05
Patent number
US05019577

Linked notes

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