1,2-Dichloroethane → 3(S)-ethyl-prolyl-methionine isopropyl ester

HRID 1779504노트

반응식

HRID 1779504 반응식
[CH2:1]([C@H:3]1[CH2:7][CH2:6][NH:5][C@@H:4]1[C:8]([OH:10])=O)[CH3:2].Cl.[CH:12]([O:15][C:16](=[O:23])[C@H:17]([CH2:19][CH2:20][S:21][CH3:22])[NH2:18])([CH3:14])[CH3:13].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C>[CH:12]([O:15][C:16](=[O:23])[C@H:17]([CH2:19][CH2:20][S:21][CH3:22])[NH:18][C:8](=[O:10])[C@@H:4]1[C@@H:3]([CH2:1][CH3:2])[CH2:7][CH2:6][NH:5]1)([CH3:14])[CH3:13]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 21156159Isopropyl L-methionate hydrochlorideHCID 54352229trans-3-Ethylproline

생성물 1

HCID 867507903(S)-ethyl-prolyl-methionine isopropyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-(t-Butyloxycarbonyl)-pyrrolidin-2(S)-ylmethyl]3(S)-ethyl-proline (2.4 g, 0.008 mol), methionine isopropyl ester hydrochloride (2.21 g, 0.0097 mol), HOBT (1.49 g, 0.0097 mol) and EDC (1.86 g, 0.0097 mol) were dissolved in DMF (15 mL) at room temperature and treated with N-methylmorpholine (3 mL, 0.024 mol). The reaction mixture was stirred overnight at room temperature, then concentrated and partitioned between EtOAc and H2O. The organic layer was washed with aq satd NaHCO3 solution, brine, and dried (MgSO4). The crude product was chromatographed on a flash silica gel column eluting with hexane: EtOAc, 7:3 to give N-(t butyloxycarbonyl)-pyrrolidin-2(S)-ylmethyl]3(S)-ethyl-prolyl-methionine isopropyl ester.

후처리

  1. concentrationconcentrated
  2. custompartitioned between EtOAc and H2O
  3. washThe organic layer was washed with aq satd NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. customThe crude product was chromatographed on a flash silica gel column
  6. washeluting with hexane

출처 및 근거

ORD 기록
ord-7e3975dcc4c141a8aab7c62a53161b8c
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05627202

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