(3S,6S,7R,8R)-3-[[(3-Hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl 2-methylpropanoate → N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide

HRID 1071006ノート

反応式

HRID 1071006 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C@@H:12]1[O:22][C:20](=[O:21])[C@@H:19]([NH:23][C:24]([C:26]2[C:31]([OH:32])=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][N:27]=2)=[O:25])[CH2:18][O:17][C:15](=[O:16])[C@H:14]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:13]1[O:42]C(C(C)C)=O>C1(C)C=CC=CC=1>[CH2:35]([C@@H:14]1[C@@H:13]([OH:42])[C@H:12]([CH3:11])[O:22][C:20](=[O:21])[C@@H:19]([NH:23][C:24]([C:26]2[C:31]([OH:32])=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][N:27]=2)=[O:25])[CH2:18][O:17][C:15]1=[O:16])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

参加物

4

反応物 2

HCID 468590(3S,6S,7R,8R)-3-[[(3-Hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl 2-methylpropanoateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 11236123N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide収率 70.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Diisobutylaluminum hydride (1.5 M in toluene, 23.3 mmol) was added dropwise to a 15° C. solution of natural product UK-2A (5.8 mmol, 3.0 g) in toluene (60 mL). The mixture was stirred an additional 15 min and quenched with EtOAc (20 mL). Hydrochloric acid (2N, 100 mL) was added slowly and stirred vigorously for 15 min. The layers were separated and the organic layer dried (MgSO4) and concentrated in vacuo to give 1.82 g (70%) of Compound 1 as a foamy, light yellow solid. Exact Mass: m/z calcd. for C22H24N2O8 [M]+=44.1533, found 444.1513. 1H-NMR data was consistent for Compound 1.

後処理

  1. customquenched with EtOAc (20 mL)
  2. additionHydrochloric acid (2N, 100 mL) was added slowly
  3. stirringstirred vigorously for 15 min
  4. customThe layers were separated
  5. dry with materialthe organic layer dried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-094d4f47993d4ffcb9c12940b358c847
出典データセット
uspto-grants-2005_06
特許番号
US06903219B2

反応ノート

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