Triethylamine → 2-[(1-Tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

HRID 1166295노트

반응식

HRID 1166295 반응식
Cl.[CH2:2]([O:4][C:5](=[O:16])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[NH2:7])[CH3:3].[C:17]([NH:24][C:25]1([C:30](O)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.CCN(CC)CC>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:16])[CH:6]([NH:7][C:30]([C:25]1([NH:24][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:31])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)[CH3:3]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724939Tyrosine ethyl ester hydrochlorideHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acid

생성물 1

HCID 700271362-[(1-Tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3.0 g (12.2 mmol) of tyrosine ethyl ester hydrochloride and 2.8 g (12.2 mmol) of N-Boc-cycloleucine are suspended in 10 mL of CH2Cl2. 1.65 g (12.2 mmol) of HOBT, 3.02 g (14.6 mmol) of DCC, and 1.7 mL (12.2 mmol) of Et3N are added, and the solution is stirred at room temperature overnight. The reaction mixture is filtered, and CH2Cl2 is removed in vacuo. The residue is taken up in EtOAc, filtered, and washed successively with 1 N HCl, water, saturated aqueous NaHCO3 solution, and brine, then dried over MgSO4, filtered, and concentrated. The residue is purified by chromatography on silica gel (50% EtOAc/hexane) to yield 2-[(1-tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid ethyl ester; 1H NMR (250 MHz, CDCl3) δ 7.97 (d, 2H), 6.7 (d, 2H), 7.51 (d, 1H), 5.58 (s, 1H), 4.70-4.80 (m, 2H), 4.12 (q, 2H), 3.02 (d, 2H), 2.07-2.35 (m, 2H), 1.60-2.00 (m, 6H), 1.40 (s, 9H), 1.20 (t, 3H).

후처리

  1. filtrationThe reaction mixture is filtered
  2. customCH2Cl2 is removed in vacuo
  3. filtrationfiltered
  4. washwashed successively with 1 N HCl, water, saturated aqueous NaHCO3 solution, and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by chromatography on silica gel (50% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-9a388783f722439faaab1a656770532b
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613782B2

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