3'-Hydroxyphenylacetic acid → HCID 68676419, 화합물

HRID 1994067노트

반응식

HRID 1994067 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 68676419HCID 68676419, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9758474a3e87468f8c1706c1219c0e6e
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652061B2

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