Beta-Aminoisobutyric Acid → CID 102512474

HRID 618576

Reaktionsgleichung

Reaktionsgleichung von HRID 618576
[OH:1][CH:2]([CH:9]([CH3:20])[CH:10](O)[CH:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][CH:4]=[CH:5][C:6]([OH:8])=[O:7].[Cl:21][C:22]1[CH:23]=[C:24]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:25][C@@H:26]([C:28]([OH:30])=O)[NH2:27].[NH2:36][CH2:37][CH:38]([CH3:42])[C:39](O)=[O:40].C(O)(=O)C(CC(C)C)O.C[C@H]1C(=O)O[C@@H](CC(C)C)C(=O)O[C@H:65]([C@@H:77]([C@H:79]2[O:81][C@@H:80]2C2C=CC=CC=2)[CH3:78])[CH2:64]C=CC(=O)N[C@H](CC2C=CC(OC)=C(Cl)C=2)C(=O)NC1.CC1C(=O)OC(CC(C)C)C(=O)OC(C(C2OC2C2C=CC=CC=2)C)CC=CC(=O)NC(CC2C=CC(OC)=C(Cl)C=2)C(=O)NC1.C[C@H]1C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@@H](/C=C/C2C=CC=CC=2)C)CC=CC(=O)N[C@H](CC2C=CC(OC)=C(Cl)C=2)C(=O)NC1.C[C@H]1C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@@H](/C=C/C2C=CC=CC=2)C)CC=CC(=O)N[C@H](CC2C=CC(OC)=CC=2)C(=O)NC1.C[C@@H]1[C@@H](O)[C@H](C2C=CC=CC=2)O[C@H]1C/C=C/C(N[C@@H](C(NC[C@H](C(OC)=O)C)=O)CC1C=CC(OC)=C(Cl)C=1)=O>CO>[CH3:64][CH2:65][C@@H:77]([C@@H:79]1[O:8][C:6](=[O:7])[CH:5]=[CH:4][CH2:3][C@@H:2]([C@@H:9](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:20])[O:1][C:39](=[O:40])[C@H:38]([CH3:42])[CH2:37][NH:36][C:28](=[O:30])[C@@H:26]([CH2:25][C:24]2[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:22]([Cl:21])[CH:23]=2)[NH:27][C:80]1=[O:81])[CH3:78]

Komponenten

11

Edukt 9

HCID 64956Beta-Aminoisobutyric AcidHCID 92779(+-)-2-Hydroxyisocaproic acidHCID 5468287(13E)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[1-(3-phenyloxiran-2-yl)ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone6×HCID 6438401Cryptophycin4×HCID 9985532Cryptophycin 62×HCID 10077879Cryptophycin 34×HCID 538202503-Chloro-O-methyl-L-tyrosineHCID 540066555,7,8-Trihydroxy-6-methyl-8-phenyl-2-octenoic acidHCID 101025283Cryptophycin 43×

Produkt 1

HCID 102512474CID 102512474

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

[α]D +54.9°(MeOH, c 0.93); UV λmax (ε) 250 (20518), 284 (3857); IR (neat) νmax 3411, 3271, 2966, 1746, 1728, 1668, 1505, 1463, 1258, 1178 cm-1 ; EIMS m/z (rel intensity) 638/640 (4.5/1.1), 412/414 (59/19), 280(17), 227 (100); high resolution EIMS m/z 638.272934 (calcd for C35H43ClN2O7, 2.9 mmu error). 1H NMR (CDCl3): amino or hydroxy acid unit δ (carbon position, multiplicity; J in Hz) 5-hydroxy-6-methyl-8-phenyl-2,7-octadienoic acid (A) 5.76 (2, d; 15.5), 6.65 (3, ddd; 15.4, 9.2 and 6.2), 2.38-2.47 (4, m), 5.08 (5,ddd; 10.6, 4.9 and 2.2), 2.58 (6, m), 1.15 (6-Me, d; 6.8), 6.07 (7, dd; 15.9 and 8.5), 6.43 (8, d; 15.9), 7.21-7.35 (10/11/12/13/14, m); 3-chloro-4methoxy-phenylalanine (B) 4.83 (2, m), 3.05(3, dd; 14.5 and 7.1), 5.65 (2-NH, d; 8.7), 3.14 (3, dd; 14.4 and 5.5), 7.21 (5, d; 2.4), 3.86 (7-OCH3, s), 6.83 (8, d; 8.3), 7.08 (9, dd; 8.3 and 2.2); 3-amino-2-methylpropionic acid (C) 2.73 (2, m), 1.23 (2-Me, d; 7.2), 3.23 (3, dt; 13.5 and 6.8), 3.56 (3, ddd; 13.5, 5.7 and 4.0), 6.85 (3-NH, dd; 7.1 and 6.2); leucic acid (D) 4.8 (2, d; 4.6), 1.86-1.89 (3, m), 0.94 (3-Me, d; 7.0), 1.20-1.26 (4, m), 1.39-1.44 (4, m), 0.77 (5, d; 7.4). 13C NMR (CDCl3) unit δ (carbon position) A 165.5 (1), 125.2 (2), 141.5 (3), 36.4 (4), 77.7 (5), 41.9 (6), 17.1 (6-Me), 129.8 (7), 131.9 (8), 136.8 (9), 128.6 (10/14), 126.2 (11/13), 127.6 (12); B 170.0 (1), 53.5 (2), 35.1 (3), 129.9 (4), 131.1 (5), 122.4 (6), 153.9 (7), 56.1 (7-OCH3), 112.2 (8), 128.5 (9); C 175.3 (1), 38.6 (2), 14.0 (2-Me), 41.4 (3); D 169.5 (1), 76.6 (2), 36.2 (3), 15.5 (3-Me), 24.2 (4), 14.0 (5).

Quellen und Nachweise

ORD-Eintrag
ord-6bd4d533b98b4700827822ff22aa461b
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952298

Verknüpfte Notizen

Wird geladen…