Boc-L-leucinol → HCID 86724445, compound

HRID 870956Notes

Reaction equation

HRID 870956 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH:5]([CH3:7])[CH3:6].Cl[C:17]1[CH:18]=[CH:19][C:20]2[C:30]3[C:25](=[CH:26][N:27]=[C:28]([NH:31][C:32](=[O:34])[CH3:33])[CH:29]=3)[CH:24]([CH3:35])[O:23][C:21]=2[CH:22]=1>>[C:32]([NH:31][C:28]1[CH:29]=[C:30]2[C:20]3[CH:19]=[CH:18][C:17]([O:1][CH2:2][C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:4][CH:5]([CH3:7])[CH3:6])=[CH:22][C:21]=3[O:23][CH:24]([CH3:35])[C:25]2=[CH:26][N:27]=1)(=[O:34])[CH3:33]

Participants

3

Reactant 2

HCID 7018766Boc-L-leucinolHCID 86695947HCID 86695947, compound

Product 1

HCID 86724445HCID 86724445, compoundYield 33%

Procedure

Prepared as described in Example 8, Part C using (S)-tert-butyl (1-hydroxy-4-methylpentan-2-yl)carbamate and N-(8-chloro-5-methyl-5H-chromeno[3,4-c]pyridin-2-yl)acetamide to afford tert-butyl ((2S)-1-((2-acetamido-5-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (290 mg, 0.617 mmol, 33% yield) as a yellow oil. LCMS (ESI) m/e 470.3 [(M+H)+, calcd for C26H36N3O5 470.3]; LC/MS retention time (Method F): tR=0.99 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3981b561f81e4952a7fc0535d54ac9e6
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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