Methyl L-phenylalaninate hydrochloride → HCID 59510439, compound

HRID 2423001Notes

Reaction equation

HRID 2423001 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(N(C(C)C)CC)(C)C.N1([C:29]([O:31][C:32]([CH3:61])([CH2:34][CH2:35][CH2:36][O:37][C:38]([C:53]2[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][CH:54]=2)([C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:33])=[O:30])C=CN=C1>CN(C)C=O>[CH3:60][O:59][C:56]1[CH:55]=[CH:54][C:53]([C:38]([C:45]2[CH:46]=[CH:47][C:48]([O:51][CH3:52])=[CH:49][CH:50]=2)([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[O:37][CH2:36][CH2:35][CH2:34][C:32]([CH3:61])([O:31][C:29]([NH:6][C@@H:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH3:2])=[O:14])=[O:30])[CH3:33])=[CH:58][CH:57]=1

Participants

5

Reactant 3

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 81531DiisopropylethylamineHCID 59510440HCID 59510440, compound

Product 1

HCID 59510439HCID 59510439, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution composed of L-phenylalanine methyl ester hydrochloride (1.4 g, 6.1 mmol), diisopropylethylamine (1.1 mL, 6.2 mmol), and N,N-dimethylformamide (40 mL) was added to the solution of Example 1. The reaction was stirred overnight at room temperature. The solvents were evaporated at reduced pressure, and then the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried over sodium sulfate, and filtered. The solvents were evaporated once again. Chromatography on silica gel eluting with hexane-ethyl acetate 70:30 afforded purified Cmoc-protected phenylalanine methyl ester. MS (EI+): 626 (M+1).

Workup

  1. customThe solvents were evaporated at reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvents were evaporated once again
  7. customChromatography on silica gel eluting with hexane-ethyl acetate 70:30 afforded
  8. custompurified Cmoc-protected phenylalanine methyl ester

Sources & evidence

ORD record
ord-4abc67377ade4dc88ced3611b267fb8b
Source dataset
uspto-grants-2011_06
Patent number
US07960526B2

Reaction notes

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