Ethanol → HCID 57595538, compound

HRID 1786002Notes

Reaction equation

HRID 1786002 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][N:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C@H:20]([N:27]([C:35](=[O:37])[CH3:36])[C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[CH2:19][C@@H:18]2[CH3:38])=[O:16])=[CH:11][CH:10]=1)[CH3:8].C(O)C.[OH-].[Li+]>O1CCCC1>[C:35]([N:27]([C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C@H:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:17]([C:15]([C:12]2[CH:13]=[CH:14][C:9]([N:7]([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]([OH:39])=[O:2])=[CH:10][CH:11]=2)=[O:16])[C@@H:18]([CH3:38])[CH2:19]1)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 57595379HCID 57595379, compound

Product 1

HCID 57595538HCID 57595538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(2S,4R)-4-[(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-methyl-amino]-butyric acid was prepared from (2S,4R)-4-[(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-methyl-amino]-butyric acid methyl ester was hydrolyzed to the acid by dissolving in tetrahydrofuran and ethanol and lithium hydroxide (1N) was added and heated 50° C. for 2 h. The mixture was cooled to room temperature, acidified to form a white precipitate. The solid was filtered to give to afford the product after HPLC purification.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customto form a white precipitate
  3. filtrationThe solid was filtered
  4. customto give
  5. customto afford the product
  6. customafter HPLC purification

Sources & evidence

ORD record
ord-016c0a28ebad401fb22e451500a15c10
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…