Hydrochloric Acid → (9-Hydroxycinchonan-6'-yl)butanimidic acid methyl ester

HRID 1599373Notes

Reaction equation

HRID 1599373 reaction equation
Cl.[OH:2][C@@H:3]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21](OCCCC#N)[CH:22]=2)[N:17]=[CH:16][CH:15]=1)[C@@H:4]1[N:9]2[CH2:10][CH2:11][C@H:6]([C@@H:7]([CH:12]=[CH2:13])[CH2:8]2)[CH2:5]1.[CH3:30][OH:31]>>[CH3:30][O:31][C:8](=[NH:9])[CH:7]([C:21]1[CH:22]=[C:23]2[C:18]([N:17]=[CH:16][CH:15]=[C:14]2[CH:3]([OH:2])[C@@H:4]2[N:9]3[CH2:10][CH2:11][C@H:6]([C@@H:7]([CH:12]=[CH2:13])[CH2:8]3)[CH2:5]2)=[CH:19][CH:20]=1)[CH2:6][CH3:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 131720616HCID 131720616, compound

Product 1

HCID 131720617(9-Hydroxycinchonan-6'-yl)butanimidic acid methyl ester

Procedure

Hydrochloric acid gas was bubbled through a solution of 200 mg (0.52 mmol) of (9S)-4-[(9-hydroxycinchonan-6'-yl)oxy]butanenitrile (2) in 5 ml of anhydrous methanol at -10° C. for a period of 15 minutes. The reaction mixture was stoppered and left at 4° C. for 4 days, concentrated to dryness and yielded 220 mg (0.49 mmol, 93%) of (9S)-4-[(9-hydroxycinchonan-6'-yl)butanimidic acid methyl ester (3) as solids. HNMR indicated the purity of (9S)-4-[(9-Hydroxycinchonan-6'-yl)butanimidic acid methyl ester (3) was 75% with the remaining 25% as the hydrolyzed compound.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bd69c629451c476b9a4c4799381c4148
Source dataset
uspto-grants-1998_04
Patent number
US05741715

Reaction notes

Loading…