1,2-Dichloroethane → N-{[7-(4-N-Boc-Piperazin-1-yl)-3,4-dihydro-1(1H)-isoquinolinone-2-yl]acetyl}-3(S)-(ethynyl)-beta-alanine ethyl ester

HRID 1377526노트

반응식

HRID 1377526 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[C:22]3[C:17]([CH2:18][CH2:19][N:20]([CH2:25][C:26](O)=[O:27])[C:21]3=[O:24])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[CH2:44]([O:46][C:47](=[O:53])[CH2:48][C@@H:49]([C:51]#[CH:52])[NH2:50])[CH3:45].CCN(CC)CC>>[CH2:44]([O:46][C:47](=[O:53])[CH2:48][C@@H:49]([C:51]#[CH:52])[NH:50][C:26](=[O:27])[CH2:25][N:20]1[CH2:19][CH2:18][C:17]2[C:22](=[CH:23][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13][CH2:12]3)=[CH:15][CH:16]=2)[C:21]1=[O:24])[CH3:45]

참가 물질

6

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11794693[7-(4-t-Butoxycarbonylpiperazin-1-yl)-3,4-dihydro-1(1H)-isoquinolinone-2-yl]acetic acidHCID 86751219Ethyl (3s)-3-aminopent-4-ynoate hydrochloride

생성물 1

HCID 86751218N-{[7-(4-N-Boc-Piperazin-1-yl)-3,4-dihydro-1(1H)-isoquinolinone-2-yl]acetyl}-3(S)-(ethynyl)-beta-alanine ethyl ester

실험 절차

To a solution of 1-5 (150 mg, 0.39 mmol), HOBT (63 mg, 0.46 mmol) and EDC (111 mg, 0.58 mmol) was added 3(S)-(ethynyl)-β-alanine ethyl ester hydrochloride (1-32) (U.S. Pat. No. 5,272,162; 82 mg, 0.46 mmol) and Et3N (80.7 gl, 0.58 mmol). The mixture was stirred at room temperature under argon for 16 hours and then partitioned between EtOAc and 10% citric acid. The aqueous phase was extracted with EtOAc (x3) and the combined organic layers then washed with saturated aqueous NaHCO3 followed by brine. Removal of the dried (MgSO4) solvent afforded a yellow oil which was purified by column chromatography (silica gel; hexane/EtOAc 1:1) to give 1-33 as an oil. Rf (silica; EtOAc/hexane 2:1) 0.57 ##STR51##

후처리

  1. custompartitioned between EtOAc and 10% citric acid
  2. extractionThe aqueous phase was extracted with EtOAc (x3)
  3. washthe combined organic layers then washed with saturated aqueous NaHCO3
  4. customRemoval of the
  5. dry with materialdried (MgSO4) solvent
  6. customafforded a yellow oil which
  7. customwas purified by column chromatography (silica gel; hexane/EtOAc 1:1)

출처 및 근거

ORD 기록
ord-c36e48a642a54f209e6ce7c3eff7d424
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665723

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