Water → (S)-3-(2-Nitro-phenylamino)-hexanoic acid ethyl ester

HRID 1747373Notes

Reaction equation

HRID 1747373 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([O:13][C:14](=[O:21])[CH2:15][C@@H:16]([NH2:20])[CH2:17][CH2:18][CH3:19])[CH3:12].C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[CH2:11]([O:13][C:14](=[O:21])[CH2:15][C@@H:16]([NH:20][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH2:17][CH2:18][CH3:19])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 10773249Ethyl (3S)-3-aminohexanoate

Product 1

HCID 59497566(S)-3-(2-Nitro-phenylamino)-hexanoic acid ethyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-fluoro-2-nitrobenzene (500 mg, 3.5 mmol) in DMF (150 mL) were added (S)-3-Amino-hexanoic acid ethyl ester (600 mg, 3.8 mmol) and diisopropyl ethylamine (0.65 mL, 3.8 mmol). The solution was heated to 90 C for 16 hours. The solution was cooled down and was water (300 mL) was added. The solution was extracted with EtOAc and the combined organic layer was dried with MgSO4. The mixture was filtered and the filtrate was concentrated. The residue was purified by CombiFlash with 5% EtOAc in Hexane as the eluent to afford the desirable product (S)-3-(2-Nitro-phenylamino)-hexanoic acid ethyl ester (795 mg, 80%) as a colorless oil.

Workup

  1. temperatureThe solution was heated to 90 C for 16 hours
  2. temperatureThe solution was cooled down
  3. additionwas added
  4. extractionThe solution was extracted with EtOAc
  5. dry with materialthe combined organic layer was dried with MgSO4
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by CombiFlash with 5% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-077cb6fd19544d829273c2e7739df948
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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