1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → {2-[5-(2-tert-Butoxycarbonylaminoethylcarbamoyl)-pentylcarbamoyl]ethyl}-carbamic acid benzyl ester

HRID 249630

반응식

HRID 249630 반응식
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34][NH2:35])=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N=C=NCCCN(C)C)C>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][CH2:13][C:14](=[O:15])[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[NH:35][CH2:34][CH2:33][NH:32][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 187201N-BOC-ethylenediamineHCID 692965966-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid

생성물 1

HCID 69296149{2-[5-(2-tert-Butoxycarbonylaminoethylcarbamoyl)-pentylcarbamoyl]ethyl}-carbamic acid benzyl ester수율 73%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The compound 37 was prepared using General Procedure B with the acid 36 2.23 g, 6.63 mmol), 2-t-butoxycarbonylamino-ethylamine (1.27 g, 7.95 mmol), 1-hydrobenzotriazole (HOBt) (1.25 g, 9.28 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (1.79 g, 9.28 mmol) in DMF (20 mL). Recrystallization of the crude product from EtOAc afforded 2.30 g (73%) of the desired product (37) as a white solid. 1H NMR (CDCl3): δ 7.32 (m, 5H, ArH), 6.44 (s, 1H, NH), 6.23 (s, 1H, NH), 5.67 (s, 1H, NH), 5.19 (s, 1H, NH), 5.06 (s, 2H, OCH2Ar), 3.45 (dt, J=6.4, 12.4 Hz, 2H, CH2NHCO), 3.31 (dt, J=5.2, 10.4 Hz, 2H, CH2NHCO), 3.21 (m, 4H, CH2NHCO), 2.39 (dt, J=6.0, 6.4 Hz, 2H, CH2CO), 2.14 (dt, J=7.0, 7.2 Hz, 2H, CH2CO), 1.60 (m, 2H, CH2), 1.47 (m, 2H, CH2), 1.41 (s, 9H, t-Bu), 1.30 (m, 2H, CH2); ESI-MS m/z 513[N+Cl]−; 501[M+Na]+, 479[M+H]+.

후처리

  1. customThe compound 37 was prepared
  2. customRecrystallization of the crude product from EtOAc

출처 및 근거

ORD 기록
ord-6aa46f12fcee482e924165f5826aff59
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07862807B2

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