Dichloromethane → (trans)-1-[[(3-Ethoxy-3-oxopropyl)ethylamino]carbonyl]-4-hydroxy-L-proline, phenylmethyl ester

HRID 485330노트

반응식

HRID 485330 반응식
ClCCl.Cl.[OH:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7]1.[CH3:21][N:22]1[CH2:27][CH2:26]O[CH2:24][CH2:23]1.OC1CN[C@H]([C:34]([O:36][CH2:37][C:38]2C=CC=CC=2)=[O:35])C1.C(OCC)(=[O:46])C>>[CH2:37]([O:36][C:34](=[O:35])[CH2:26][CH2:27][N:22]([CH2:23][CH3:24])[C:21]([N:9]1[CH2:10][C@H:6]([OH:5])[CH2:7][C@H:8]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:46])[CH3:38]

참가 물질

6

반응물 5

HCID 6344Dichloromethane2회HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 139375174-hydroxy-L-proline, phenylmethyl esterHCID 16212860Benzyl (4R)-4-hydroxy-L-prolinate--hydrogen chloride (1/1)

생성물 1

HCID 131714305(trans)-1-[[(3-Ethoxy-3-oxopropyl)ethylamino]carbonyl]-4-hydroxy-L-proline, phenylmethyl ester

실험 절차

This residue is dissolved in 30 ml. of dichloromethane and (trans)-4-hydroxy-L-proline, phenylmethyl ester, hydrochloride (6.9 g., 1.2 eq.) is added. To the resulting suspension is added dropwise N-methylmorpholine (5.6 ml., 2.4 eq.) in 20 ml. of dichloromethane. The resulting mixture is stirred at room temperature for 15 hours. The solvent is removed at reduced pressure and the residue taken up in ethyl acetate. This is washed with water (twice), 1N hydrochloric acid (twice), 1N sodium bicarbonate (twice), and once with brine. After drying (MgSO4), the solvent is removed at reduced pressure. The residue is flash chromatographed (Whatman silica gel LPS-1, hexane:ethyl acetate; 65:35) to give 7.72 g. of (trans)-1-[[3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-4-hydroxy-L-proline, phenylmethyl ester as a colorless oil; TLC (silica gel, ethyl acetate) Rf =0.34.

후처리

  1. dissolutionThis residue is dissolved in 30 ml
  2. customThe solvent is removed at reduced pressure
  3. washThis is washed with water (twice), 1N hydrochloric acid (twice), 1N sodium bicarbonate (twice), and once with brine
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent is removed at reduced pressure
  6. customchromatographed (Whatman silica gel LPS-1, hexane:ethyl acetate; 65:35)
  7. customto give 7.72 g

출처 및 근거

ORD 기록
ord-207a0729442548fcb09265955604ecc1
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04536501

반응 노트

불러오는 중…