3-(4-Hydroxyphenyl)propionic acid → 2-[3-(4-Hydroxyphenyl)propionylamino]acetic acid ethyl ester

HRID 1178069

反応式

HRID 1178069 の反応式
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([OH:21])=O)=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:45]([O:47][C:48](=[O:51])[CH2:49][NH2:50])[CH3:46]>CN(C=O)C.O>[CH2:45]([O:47][C:48](=[O:51])[CH2:49][NH:50][C:19](=[O:21])[CH2:18][CH2:17][C:14]1[CH:13]=[CH:12][C:11]([OH:10])=[CH:16][CH:15]=1)[CH3:46]

参加物

8

反応物 5

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 102641582-[3-(4-Hydroxyphenyl)propionylamino]acetic acid ethyl ester収率 130%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (390 mg, 0.52 mL, 3.02 mmol) was added to a stirred solution of 3-[4-hydroxy phenyl]propionic acid (100 mg, 0.60 mmol) in DMF (10 mL). HOBT (90 mg, 0.67 mmol) and EDCI.HCl (290 mg, 1.51 mmol) were added at room temperature. After 2 minutes glycine ethyl ester hydrochloride (100 mg, 0.72 mmol) was added. The resulting mixture was stirred at room temperature for 48 hours. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 196 mg of [3-(4-hydroxy-phenyl) propionylamino]-acetic acid ethyl ester. 1H NMR (CDCL3): δ 7 (d, 2H), 6.65 (d, 2H), 6.0 (bs, 1H), 4.15 (q, 2H), 4.0 (d, 2H), 3.5 (s, 2H), 2.8 (t, 2H), 2.45 (t, 2H), 1.2 (t, 3H), LC-MS purity: 68.23%.

後処理

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d37264a6fbb144a8a5e7942dea211699
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

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