Beta-Alanine → HCID 178445780, compound

HRID 713896Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([O:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:16][CH2:15]1)[CH:7]=[CH:6]2)=O.[NH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].C([BH3-])#N.[Na+]>>[C:20]([C@H:17]1[CH2:18][CH2:19][C@H:14]([O:13][C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([CH2:1][NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:4]=3)[N:9]=2)[CH2:15][CH2:16]1)([CH3:23])([CH3:22])[CH3:21]

Participants

Reactant 3

HCID 239Beta-Alanine

HCID 5003444Sodium cyanoborohydride

HCID 178445789HCID 178445789, compound

Product 1

HCID 178445780HCID 178445780, compound

Procedure

6-bromo-2-hydroxyquinoline was treated with cis-4-tert-butylcyclohexanol under Mitsunobu conditions, affording 6-bromo-2-((trans)-4-tert-butylcyclohexyloxy)quinoline. 6-bromo-2-((trans)-4-tert-butylcyclohexyloxy)quinoline was then exposed to n-butyllithium and DMF, providing 6-formyl-2-((trans)-4-tert-butylcyclohexyloxy)quinoline. This aldehyde was then treated with 3-aminopropionic acid and sodium cyanoborohydride to afford the title compound, 3-((2-((trans)-4-tert-butylcyclohexyloxy)quinolin-6-yl)methylamino)propanoic acid.

Sources & evidence

ORD record: ord-6b37482a2dcb42a7a2d7c8fbda32ebf8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186367B2

Reaction notes

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