1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Cbz-Asp(OBut)-Gly-OBn

HRID 964491

반응식

HRID 964491 반응식
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].Cl.[NH2:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>ClCl.C(Cl)Cl>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([NH:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[O:13])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 11701227Benzyl 2-aminoacetate hydrochloride

생성물 1

HCID 14375963Cbz-Asp(OBut)-Gly-OBn수율 108.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24526Chlorine용매

실험 절차

A mixture of Cbz-Asp(OBut)-OH (3590 mg, 11.1 mmol), HCl+H-Gly-OBn (3360 mg, 16.6 mmol), EDCI (3180 mg, 16.6 mmol), HOBt (2250 mg, 16.6 mmol) and DIEA (2900 mg, 16.6 mmol) in dry CH2 Cl2 (50 mL) was stirred at r.t. for six hours. The reaction mixture was added CH2Cl2 (150 mL) and washed with 1N HCl (200 mL), saturated NaHCO3 aq. (200 mL) and brine (200 mL). The organic layer was passed through an inch of SiO2 layer and the SiO2 was washed with 1/9=AcOEt/CH2Cl2 (200 mL). The eluent was evaporated in vacuo to give clear oil (5690 mg, 100%): 1H NMR (300 MHz, CDCl3) δ 7.368 (s, 10H), 7.082 (t, 1H), 6.013 (d, J=7.8 Hz, 1H), 5.164 (s, 2H), 5.126 (s, 2H), 4.592 (d, J=6.6 Hz, 1H), 4.072 (d, J=5.7 Hz, 2H), 2.891 (dd, J=18.2, 4.5 Hz, 1H), 2.641 (dd, J=17.1, 6.3 Hz, 1H), 1.423 (s, 9H); 13C NMR (300 MHz, CDCl3) δ 171.0, 170.9, 169.3, 136.1, 135.2, 129.7, 128.6 (2C), 128.4, 128.3, 128.2, 81.9, 67.3, 67.2, 51.1, 41.5, 37.3, 28.0.

후처리

  1. washwashed with 1N HCl (200 mL), saturated NaHCO3 aq. (200 mL) and brine (200 mL)
  2. washthe SiO2 was washed with 1/9=AcOEt/CH2Cl2 (200 mL)
  3. customThe eluent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-874846bbe82a4e449dc38c8d22cfa6f1
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770380

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