4-Methoxybenzaldehyde → 3-Benzyl-6-benzyloxymethyl-1-(4-methoxybenzyl)-(3S, 6S)-perhydro-2,5-pyrazinedione

HRID 399098

反応式

HRID 399098 の反応式
[NH:1]([C:13]([O:15]CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([CH:38]=O)=[CH:36][CH:37]=1.[NH:40](C(OC(C)(C)C)=O)[C@H:41](C(O)=O)[CH2:42][O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C1C=NC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>>[CH2:3]([C@@H:2]1[NH:1][C:13](=[O:15])[C@H:41]([CH2:42][O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[N:40]([CH2:38][C:35]2[CH:36]=[CH:37][C:32]([O:31][CH3:30])=[CH:33][CH:34]=2)[C:10]1=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 4

HCID 312444-MethoxybenzaldehydeHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 978331Fmoc-phenylalanineHCID 131720865HOAt DIC

生成物 1

HCID 573036703-Benzyl-6-benzyloxymethyl-1-(4-methoxybenzyl)-(3S, 6S)-perhydro-2,5-pyrazinedione

実験手順

TentaGel resin was coupled with FmocPhe (Mitsunobu conditions) and reductively alkylated with anisaldehyde. BocSer(OBzl) was coupled with HOAt/DIC and after Boc-deprotection the DKP formed in 4% TEA/toluene (12 h). Yield: 7.1 mg (8.3%). 1H-NMR (400 MHz, CDCl3): δ=1.60 (dd, J=6.4, 6.4 Hz, 1 H), 3.22 (dd, J=3.4, 10.0 Hz, 1 H), 3.28 (dd, J=2.8, 10.0 Hz, 1 H), 3.44 (dd, J=2.2, 6.4 Hz, 1 H), 3.81 (s, 3 H), 3.85 (d, J=14.6 Hz, 1 H), 4.07 (dd, J=2.2, 6.4 Hz, 1 H), 4.18 (dd, J=2.8 3.4 Hz, 1 H), 4.21 (d, J=8.0 Hz, 1 H), 4.25 (d, J=8.0 Hz, 1 H), 5.54 (d, J=14.6 Hz, 1 H), 6.42 (broad s, 1 H), 6.87-6.89 (m, 2 H), 7.19-7.40 (m, 12 H). 13C-NMR (101 MHz, CDCl3): δ=36.6, 46.5, 55.8, 59.0, 72.1, 73.5, 114.6, 126.9, 127.8, 128.0, 128.2, 128.7, 129.1, 130.2, 130.5, 135.2, 137.4, 159.8, 163.5, 166.7. Anal. Calcd. for C27H28 N2O4.2H2O: C, 67.48; H, 6.71; N, 5.83, found: C, 68.00; H, 6.18; N, 5.65.

出典と根拠

ORDレコード
ord-6b794abab66644579aebc93e57d90aa2
出典データセット
uspto-grants-1998_10
特許番号
US05817751

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