Methyl L-phenylalaninate hydrochloride → HCID 68770629, compound

HRID 2265172Notes

Reaction equation

HRID 2265172 reaction equation
Cl[C:2]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:4]2[C:5]([O:7]C(=O)[NH:9][C:3]=12)=O.[ClH:15].[CH3:16][O:17][C:18](=[O:28])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:20]>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:16][O:17][C:18](=[O:28])[CH:19]([NH:20][C:5](=[O:7])[C:4]1[CH:11]=[C:12]([Cl:15])[C:13]([Cl:14])=[CH:2][C:3]=1[NH2:9])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 33730957HCID 33730957, compound

Product 1

HCID 68770629HCID 68770629, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

3,4-Dichloroisatoic anhydride (147 mg, 0.634 mmol) was dissolved in DMF (2 mL). (L)-Phenylalanine methyl ester hydrochloride (150 mg, 0.697 mmol) and DMAP (85 mg, 0.697 mmol) were added and the mixture was stirred overnight at rt. The mixture was quenched with water and extracted with EtOAc (3×). The combined organic layers were washed with water, dried (MgSO4), filtered and concentrated to provide the crude product. The crude solid was purified by flash chromatography (hexanes/EtOAc) to provide the desired product as a white solid (150 mg, 68%). 1H NMR (400 MHz, CDCl3): 7.27-7.21 (m, 5H), 7.07-7.05 (m, 2H), 6.30 (d, J=7.2, 1H), 5.44 (br s, 2H), 4.95-4.90 (m, 1H), 3.71 (s, 3H), 3.22-3.09 (m, 2H).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide the crude product
  8. customThe crude solid was purified by flash chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-1d6119a0a47d48baa92d06728d0e8b4a
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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