Boc-L-leucinol → HCID 86724432, compound

HRID 870927Notes

Reaction equation

HRID 870927 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](=[C:26]([NH:31][C:32](=[O:34])[CH3:33])[N:27]=[CH:28][CH:29]=3)[CH:24]([CH3:35])[O:23][C:21]=2[CH:22]=1>>[C:32]([NH:31][C:26]1[N:27]=[CH:28][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]=12)(=[O:34])[CH3:33]

Participants

3

Reactant 2

HCID 7018766Boc-L-leucinolHCID 86724433HCID 86724433, compound

Product 1

HCID 86724432HCID 86724432, compoundYield 51%

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-4-yl)acetamide to afford tert-butyl ((2S)-1-((4-acetamido-5-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (0.6 g, 0.882 mmol, 51% yield) as a yellow solid. LCMS (ESI) m/e 470.2 [(M+H)+, calcd for C26H36N3O5 470.3]; LC/MS retention time (Method C): tR=1.89 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4b11193a9b674e109bed037ec048ab22
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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