Water → 4(Aminomethyl)-2-phenylbenzoyl methionine methyl ester

HRID 2121245Notes

Reaction equation

HRID 2121245 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]=[N+]=[N-])=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH3:5].[C:3]([O:2][CH2:1][CH3:29])(=[O:28])[CH3:4].[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 20622822HCID 20622822, compound

Product 2

HCID 18464838Ammonia ethyl acetateYield 1%HCID 206228204(Aminomethyl)-2-phenylbenzoyl methionine methyl esterYield 193.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 332B (1.00 g, 2.5 mmol) and triphenylphosphine (0.98 g, 3.75 mmol) in THF (10 mL) was heated at reflux for 4 hours. The reaction mixture was cooled to ambient temperature, water (0.45 mL) was added, and the reaction mixture was stirred for 18 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel (25% ethyl acetate-hexane, then 1% ammonia-ethyl acetate) gave the desired compound as a colorless oil (900 mg, 97%).

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80f5081cefb64f189b8422d3db18724d
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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