Boc-L-leucinol → HCID 86724453, compound

HRID 870972Notes

Reaction equation

HRID 870972 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: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:34]([NH:33][C:30]1[CH:31]=[C:32]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]([O:23][CH3:24])[C:21]=3[O:25][CH2:26][C:27]2=[CH:28][N:29]=1)(=[O:36])[CH3:35]

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 (S)-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 (S)-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-ea2abf019665401c94f23a5a8b1828ef
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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