Boc-L-leucinol → HCID 86724451, compound

HRID 870966Notes

Reaction equation

HRID 870966 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:31]3[C:26](=[CH:27][N:28]=[C:29]([NH:32][C:33](=[O:35])[CH3:34])[CH:30]=3)[CH2:25][O:24][C:21]=2[C:22]=1[CH3:23]>>[C:33]([NH:32][C:29]1[CH:30]=[C:31]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])=[C:22]([CH3:23])[C:21]=3[O:24][CH2:25][C:26]2=[CH:27][N:28]=1)(=[O:35])[CH3:34]

Participants

3

Reactant 2

HCID 7018766Boc-L-leucinolHCID 86724452HCID 86724452, compound

Product 1

HCID 86724451HCID 86724451, compoundYield 11%

Procedure

Prepared as described in Example 8, Part C using (S)-tert-butyl (1-hydroxy-4-methylpentan-2-yl)carbamate and N-(8-chloro-7-methyl-5H-chromeno[3,4-c]pyridin-2-yl)acetamide to afford (S)-tert-butyl (1-((2-acetamido-7-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (168 mg, 0.037 mmol, 11% yield) as a brown oil. LCMS (ESI) m/e 470.3 [(M+H)+, calcd for C26H36N3O5 470.3]; LC/MS retention time (Method F): tR=0.96 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-13f3de50ea9a44648e99d7e8b1bedf26
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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