Ethyl Acetate → Acetylphenylalanine methyl ester

HRID 1821539Notes

Reaction equation

HRID 1821539 reaction equation
[H][H].[CH3:3][O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:7].[C:16](OCC)(=[O:18])[CH3:17]>CO.[B-](F)(F)(F)F.CC[C@H]1CC[C@H](CC)P1C1C(P2[C@@H](CC)CC[C@@H]2CC)=CC=CC=1.C1CC=CCCC=C1.[Rh]>[CH3:3][O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH:7][C:16](=[O:18])[CH3:17]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 736234L-Phenylalanine, methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 704002Acetylphenylalanine methyl ester

Reagents, catalysts & solvents 2

HCID 11006841(+)-1,2-Bis((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(l)tetrafluoroborateCatalystHCID 887MethanolSolvent

Procedure

The synthesis was carried out with reference to the disclosure of Reference Article (7). There was dissolved 1.46 g (6.4 mmol) of the dehydro-compound (30) in 20 ml of dehydrated methanol, 35 mg of (S,S)-Et-DuPhos-Rh catalyst was introduced into the solution and the resulting mixture was stirred at room temperature for 16 hours using a medium pressure reducing device at a hydrogen gas pressure of 2 atm. The resulting product was loaded on a silica gel column (20×55 mm), followed by elution with 200 ml of ethyl acetate to thus give 1.40 g (6.0 mmol, 95%) of the intended compound: phenylalanine methyl ester (3).

Workup

  1. additionwas introduced into the solution

Sources & evidence

ORD record
ord-cb4729718d9a48138d540ab04883797d
Source dataset
uspto-grants-2009_10
Patent number
US07608248B2

Reaction notes

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