L-Phenylalanine, methyl ester → HCID 59364047, compound

HRID 2380759Notes

Reaction equation

HRID 2380759 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]([OH:14])=O)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.[CH3:27][O:28][C:29](=[O:39])[C@H:30]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[NH2:31]>CN(C=O)C>[CH3:27][O:28][C:29](=[O:39])[CH:30]([NH:31][C:12]([C:9]1[S:10][CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)=[O:14])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 736234L-Phenylalanine, methyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 38785394-Phenylthiazole-2-carboxylic acid

Product 1

HCID 59364047HCID 59364047, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 4-Phenyl-thiazole-2-carboxylic acid (100 mg, 0.4 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.44 mmol) in DMF (4 mL) at 25° C. was added phenylalanine methyl ester (72 mg, 0.4 mmol), the resulting mixture was stirring at 25° C. for overnight and concentrated in vacuo, and the residue was dissolved in CH2Cl2 (20 mL) was washed with 5% NaHCO3, dried with MgSO4 and concentrated in vacuo. The residue was purified by HPLC. The product was obtained 92 mg (61%) as white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (20 mL)
  3. washwas washed with 5% NaHCO3
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC
  7. customThe product was obtained 92 mg (61%) as white solid

Sources & evidence

ORD record
ord-62092a5053954f6fadbf8dce08b598d8
Source dataset
uspto-grants-2012_09
Patent number
US08257931B2

Reaction notes

Loading…