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Triethylamine → Tert-butyl 2-(4-nitrophenylamino)propionate

HRID 131053
Notes
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Reaction equation

HRID 131053 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([O:15][C:16](=[O:20])[C@H:17]([CH3:19])[NH2:18])([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC.CN1CCCC1=O>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:18][CH:17]([CH3:19])[C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:20])=[CH:3][CH:4]=1)([O-:10])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 13387N-methyl-2-pyrrolidoneHCID 89016L-Alanine 1,1-dimethylethyl ester

Product 1

HCID 58596136Tert-butyl 2-(4-nitrophenylamino)propionateYield 33.6%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
70 °C

Procedure

388 mg of 4-fluoronitrobenzene, 500 mg of L-alanine tert-butyl ester and 0.9 ml of Et3N were added to a solution of 10 ml of N-methylpyrrolidinone. The reaction medium was heated at 70° C. for 20 hours and, after cooling to room temperature, then poured into a water and ice mixture. The yellow precipitate formed was filtered off, re-slurried in water and then dried over P2O5. 246 mg of tert-butyl 2-(4-nitrophenylamino)propionate (10) were obtained.

Workup

  1. temperatureafter cooling to room temperature
  2. customThe yellow precipitate formed
  3. filtrationwas filtered off, re-slurried in water
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-79adefcb38fd4457bda61c8c9d8bb863
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07384432B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes