(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 895796노트

반응식

HRID 895796 반응식
[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>C(Cl)Cl>[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

참가 물질

4

반응물 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

생성물 1

HCID 11236123N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide수율 70.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diisobutylaluminum hydride (1.0 M in CH2Cl2, 23.3 mmol) was added dropwise to a 20° C. solution of natural product UK-2A (1) (5.8 imol, 3.0 g) in CH2Cl2 (60 mL). The mixture was stirred an additional 15 min and quenched with EtOAc (10 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 3 as a foamy, light yellow solid. 1H NMR (300 MHz, CDCl3): δ 11.82 (s, 1H), 8.63 (d, J=8.2 Hz, 1H), 8.01 (d, J=5.2 Hz, 1H), 7.32-7.20 (m, 5H), 6.89 (d, J=5.2 Hz), 5.35 (m, 1H), 5.16 (m, 1H), 4.86 (m, 1H), 3.96 (s, 3H), 3.76 (t, J=9.4 Hz, 1H), 3.62 (m, 1H), 3.25 (m, 1H), 3.02 (m, 1H), 2.77 (m, 1), 1.51 (d, J=6.3 Hz, 3H); 13C NMR (MHz, CDCl3): δ 173.2, 170.2, 169.4, 155.8, 149.2, 141.1, 138.8, 130.3, 129.2, 129.0, 127.0, 110.1, 77.6, 77.2, 65.4, 56.5, 54.4, 50.3, 35.4, 18.7 ppm; IR (KBr pellet): 3370 (br), 2966, 1751, 1654, 1529, 1453, 1263, 1045, 801 cm−1; Exact Mass: n/z calcd. for C22H24N2O8 [M]+=444.1533, found 444.1513.

후처리

  1. customquenched with EtOAc (10 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

출처 및 근거

ORD 기록
ord-96356a440da94e90a5661295964d7278
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916932B2

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