8-Phenyloctanoic acid → (RS)-5-(4-Benzyloxy-phenyl)-4-(8-phenyl-octanoylamino)-pentanoic acid ethyl ester

HRID 852884

Reaktionsgleichung

Reaktionsgleichung von HRID 852884
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([O:19][C:20](=[O:47])[CH:21]=[CH:22][CH:23]([NH:39]C(OC(C)(C)C)=O)[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:26]=1)[CH3:18]>>[CH2:17]([O:19][C:20](=[O:47])[CH2:21][CH2:22][CH:23]([NH:39][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:26]=1)[CH3:18]

Komponenten

3

Edukt 2

HCID 5202738-Phenyloctanoic acidHCID 69416006(RS)-5-(4-Benzyloxy-phenyl)-4-tertbutoxycarbonylamino-pent-2-enoic acid ethyl ester

Produkt 1

HCID 69415689(RS)-5-(4-Benzyloxy-phenyl)-4-(8-phenyl-octanoylamino)-pentanoic acid ethyl ester

Versuchsvorschrift

From 8-phenyloctanoic acid 71c and (RS)-5-(4-Benzyloxy-phenyl)-4-tertbutoxycarbonylamino-pent-2-enoic acid ethyl ester 77 (96% yield): 1H nmr (CDCl3) δ 1.20 (t, J=7.1 Hz, 3H), 1.27-1.55 (m, 10H), 2.06 (t, J=7.4 Hz, 2H), 2.52 (t, J=7.4 Hz, 2H), 2.74-2.79 (m, 2H), 4.10 (q, J=7.0 Hz, 2H), 4.84-4.88 (m, 1H), (4.94, s, 2H), 5.80 (br d, J=15.8 Hz, 1H), 6.00 (d J=8.2 Hz, 1H), 6.82-7.36 (m, 15H). 13C nmr (CDCl3) δ 172.5, 165.9, 157.5, 147.2, 142.5, 136.7, 130.1, 128.6, 128.3, 128.1, 128.0, 127.7, 127.2, 121.0, 114.7, 69.7, 60.2, 50.6, 39.3, 36.3, 35.7, 31.2, 29.0, 28.9, 28.1, 25.4, 14.0.

Quellen und Nachweise

ORD-Eintrag
ord-2eb20e9fcb054e48a2cbc60b0379f432
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253194B2

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