Boc-L-leucinol → HCID 86724453, compound

HRID 2369565Notes

Reaction equation

HRID 2369565 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[CH:18]=[CH:19][C:20]2[C:32]3[C:27](=[CH:28][N:29]=[C:30]([NH:33][C:34](=[O:36])[CH3:35])[CH:31]=3)[CH2:26][O:25][C:21]=2[C:22]=1[O:23][CH3:24]>>[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]([CH2:11][CH:12]([CH3:13])[CH3:14])[CH2:9][O:10][C:17]1[CH:18]=[CH:19][C:20]2[C:32]3[C:27](=[CH:28][N:29]=[C:30]([NH:33][C:34](=[O:36])[CH3:35])[CH:31]=3)[CH2:26][O:25][C:21]=2[C:22]=1[O:23][CH3:24])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 7018766Boc-L-leucinolHCID 86724454HCID 86724454, compound

Product 1

HCID 86724453HCID 86724453, compoundYield 60%

Procedure

Prepared as described in Example 18, Part H using (5)-tert-butyl(1-hydroxy-4-methylpentan-2-yl)carbamate and N-(8-chloro-7-methoxy-5H-chromeno[3,4-c]pyridin-2-yl)acetamide to afford (5)-tert-butyl(1-((2-acetamido-7-methoxy-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (112 mg, 0.089 mmol, 60% yield) as a brown oil. LCMS (ESI) m/e 486.2 [(M+H)+, calcd for C26H36N3O6 486.2]; LC/MS retention time (Method F): tR=0.91 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-16dd90883cab4bb1a8c9237e78b02189
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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