(E)-7-Pyridin-3-yl-hept-6-enoic acid → (RS)-5-(4-Benzyloxy-phenyl)-4-(7-pyridin-3-yl-heptanoylamino)-pentanoic acid methyl ester

HRID 852885

반응식

HRID 852885 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[CH:2]=1.[CH3:16][O:17][C:18](=[O:45])[CH:19]=[CH:20][CH:21]([NH:37]C(OC(C)(C)C)=O)[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1>>[CH3:16][O:17][C:18](=[O:45])[CH2:19][CH2:20][CH:21]([NH:37][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:25][CH:24]=1

참가 물질

3

반응물 2

HCID 13417279(E)-7-Pyridin-3-yl-hept-6-enoic acidHCID 69415650(RS)-5-(4-Benzyloxy-phenyl)-4-tertbutoxycarbonylamino-pent-2-enoic acid methyl ester

생성물 1

HCID 69414888(RS)-5-(4-Benzyloxy-phenyl)-4-(7-pyridin-3-yl-heptanoylamino)-pentanoic acid methyl ester수율 26%

실험 절차

Isolated as a gum from (E)-7-Pyridin-3-yl-hept-6-enoic acid 76 (137 mg, 0.67 mmol) and (RS)-5-(4-Benzyloxy-phenyl)-4-tertbutoxycarbonylamino-pent-2-enoic acid methyl ester RS-40 (250 mg, 0.61 mmol) to afford the title compound (79.4 mg, 26%) as a gum: chromatographed on silica using 70:30 EtOAc:petroleum. 1H nmr (CDCl3) δ 1.30 (m, 4H), 1.49-1.82 (m, 5H), 1.82-1.95 (m, 1H), 2.08 (t, J=8 Hz, 2H), 2.34 (m, 2H), 2.59 (t, J=8 Hz), 2.69 (dd, J=7, 14 Hz, 1H), 2.77 (dd, J=7, 14 Hz, 1H), 3.65 (s, 3H), 4.15 (m, 1H), 5.03 (s, 2H), 5.36 (br d, J=9 Hz, 1H), 6.90 (d, J=9 Hz, 2H), 7.9 (d, J=9 Hz, 2H), 7.17-7.52 (m, 7H), 8.42 (br s, 2H). ESMS 503 (M+H)+.

출처 및 근거

ORD 기록
ord-0bc3dcbe3cbe4793b27c031666bf90a4
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253194B2

연결된 노트

불러오는 중…