3'-Hydroxyphenylacetic acid → HCID 68676419, compound

HRID 1994067Notes

Reaction equation

HRID 1994067 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:13][O:14][C:15](=[O:21])[C@@H:16]1[CH2:20][CH2:19][CH2:18][NH:17]1.ON1C2C=CC=C[C:26]=2N=N1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:13]([O:14][C:15]([C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1)=[O:21])[CH3:26]

Participants

8

Reactant 4

HCID 121223'-Hydroxyphenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 68676419HCID 68676419, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-hydroxy phenylacetic acid (1.52 g, 10.0 mmol) in 10 mL of DCM is added L-proline methyl ester hydrochloride (1.80 g, 10.0 mmol) followed by the addition of TEA (1.67 mL, 12 mmol), 1-hydroxybenzotriazole (HOBt, 1.17 g, 10 mmol), and EDCl (1.92 g, 10 mmol). The mixture is stirred at RT for 4 days. Ethyl acetate and water is added, and the organic layer is separated and washed with brine, dried over anhydrous sodium sulfate, and concentrated. The crude mixture is purified by flash chromatography (silica gel) eluting with hexane:ethyl acetate (1:2) to give (R)-1-[2-(3-hydroxy-phenyl)-acetyl]-pyrrolidine-2-carboxylic acid ethyl ester as an oil.

Workup

  1. customthe organic layer is separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude mixture is purified by flash chromatography (silica gel)
  6. washeluting with hexane:ethyl acetate (1:2)

Sources & evidence

ORD record
ord-9758474a3e87468f8c1706c1219c0e6e
Source dataset
uspto-grants-2010_01
Patent number
US07652061B2

Reaction notes

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