HCID 10282284, compound → N-[(3S, 7R, 8R, 9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl]-3-(benzyloxy)-4-methoxypyridine-2-carboxamide

HRID 895795Notes

Reaction equation

HRID 895795 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.CC(C)C([O:15][C@@H:16]1[C@@H:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](=[O:32])[O:22][CH2:21][C@H:20]([NH:33][C:34]([C:36]2[C:41]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[C:40]([O:50][CH3:51])[CH:39]=[CH:38][N:37]=2)=[O:35])[C:19](=[O:52])[O:18][C@H:17]1[CH3:53])=O>C(Cl)Cl>[CH2:25]([C@@H:24]1[C@@H:16]([OH:15])[C@H:17]([CH3:53])[O:18][C:19](=[O:52])[C@@H:20]([NH:33][C:34]([C:36]2[C:41]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[C:40]([O:50][CH3:51])[CH:39]=[CH:38][N:37]=2)=[O:35])[CH2:21][O:22][C:23]1=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 10282284HCID 10282284, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 86594190N-[(3S, 7R, 8R, 9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl]-3-(benzyloxy)-4-methoxypyridine-2-carboxamideYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminum hydride (1.0 M in CH2Cl2, 24.8 mmol) was added dropwise to a −78° C. solution of (2) (8.27 mmol, 5.0 g) in CH2Cl2 (40 mL). The mixture was stirred an additional 15 min, quenched with EtOAc (200 mL) and warmed to ambient temperature. 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. The residue was purified by chromatography (1% acetic acid/acetone) to give 1.54 g (35%) of 4 as a glassy, white solid, m.p. 110-114° C. 1H-NMR and MS (M+1 535) were consistent with the desired product.

Workup

  1. customquenched with EtOAc (200 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
  7. customThe residue was purified by chromatography (1% acetic acid/acetone)

Sources & evidence

ORD record
ord-6620458615514cd982e0972beca24044
Source dataset
uspto-grants-2005_07
Patent number
US06916932B2

Reaction notes

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