3-Methylbutanal → 3-[5-Benzyl-1-isopentyl-3,6-dioxo-(2R, 5R)-perhydro-2-pyrazinyl]propanoic acid

HRID 399097

反応式

HRID 399097 の反応式
[NH:1]([C:15](OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@@H:2](C(O)=O)[CH2:3][CH2:4][C:5](=[O:11])[O:6]C(C)(C)C.C(=O)[CH2:33][CH:34]([CH3:36])[CH3:35].[NH:38]([C:50]([O:52]C(C)(C)C)=O)[C@@H:39]([C:47]([OH:49])=O)[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C1C=NC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>O>[CH2:40]([C@@H:39]1[C:47](=[O:49])[N:1]([CH2:15][CH2:33][CH:34]([CH3:36])[CH3:35])[C@H:2]([CH2:3][CH2:4][C:5]([OH:6])=[O:11])[C:50](=[O:52])[NH:38]1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

参加物

6

反応物 4

HCID 115523-MethylbutanalHCID 637610Boc-D-phenylalanineHCID 7018822(2R)-5-(tert-butoxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-oxopentanoic acidHCID 131720865HOAt DIC

生成物 1

HCID 1017058823-[5-Benzyl-1-isopentyl-3,6-dioxo-(2R, 5R)-perhydro-2-pyrazinyl]propanoic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Hydroxymethyl PAM resin was coupled with Fmoc-D-Glu(OtBu)-OH (Mukaiyama conditions) and reductively alkylated with isovaleraldehyde. Boc-D-Phe was coupled with HOAt/DIC and after Box-deprotection the DKP formed in 4% TEA/toluene (12h). Yield: 88 mg (37%). 1H-NMR (400 MHz, CD3 OD):δ=0.67-0.70 (m, 1 H), 1.09 (2 d, J=6.5 Hz, 6 H), 1.49-1.73 (m, 3 H), 1.80-1.90 (m, 1 H), 2.01-2.10 (m, 1 H), 2.15-2.32 (m, 1 H), 3.13 (dd, J=4.5, 13.7 Hz, 1 H), 3.19 (ddd, J=5.1, 10.1, 15.1 Hz, 1 H), 3.39 (dd, J=5.2, 13.7 Hz, 1 H), 3.81 (ddd, J=5.5, 9.6, 15.1 Hz, 1 H), 3.92 (dd, J=3.6, 9.6 Hz, 1 H), 4.41 (dd, J=5.2, 5.5 Hz, 1 H), 7.30-7.48 (m, 5 H). 13C-NMR (101 MHz, CD3OD): δ=22.8, 27.4, 29.0, 31.1, 36.8, 40.8, 44.8, 57.9, 59.7, 128.5, 129.7, 131.4, 167.3, 169.1, 177.0. Anal. Calcd. for C16H26N2O4.2 H2O: C, 59.67; H, 7.91; N, 8.09, found: C, 59.09; H, 7.06; N, 7.31.

出典と根拠

ORDレコード
ord-7503e2eb04f543a581d954559d8444b4
出典データセット
uspto-grants-1998_10
特許番号
US05817751

関連ノート

読み込み中…