Lithium Hydroxide → HCID 178483653, compound

HRID 1063652Notes

Reaction equation

HRID 1063652 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][N:7]([C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH2:18][N:19]([C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[O:22])[CH3:20])[CH2:13][CH2:12]1)=[O:10])[CH3:8])C.[Li+].[OH-]>C1COCC1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][C:21]([N:19]([CH3:20])[CH2:18][CH2:17][C@H:14]2[CH2:13][CH2:12][C@H:11]([C:9]([N:7]([CH3:8])[CH2:6][CH2:5][C:4]([OH:31])=[O:3])=[O:10])[CH2:16][CH2:15]2)=[O:22])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178472032HCID 178472032, compound

Product 1

HCID 178483653HCID 178483653, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) and stirred solution of 0.39 g (0.87 mmol) of trans-3-[(4-{2-[(4-chloro-phenoxycarbonyl)-methyl-amino]-ethyl}-cyclohexanecarbonyl)-methyl-amino]-propionic acid ethyl ester in 2.6 mL of THF was added within 5 min 2.6 mL (2.6 mmol, 3 eq) of aqueous 1M LiOH and the solution was stirred at RT for 2.5 h. The reaction was partitioned between Et2O (×3)/aqueous 10% KHSO4. The organic phase was washed with 10% NaCl, dried over Na2SO4 and evaporated to yield 0.38 g (quantitative) of trans-3-[(4-{2-[(4-chloro-phenoxycarbonyl)-methyl-amino]-ethyl}-cyclohexanecarbonyl)-methyl-amino]-propionic acid, MS: 425 (MH+, 1Cl).

Workup

  1. customThe reaction was partitioned between Et2O (×3)/aqueous 10% KHSO4
  2. washThe organic phase was washed with 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-5e4c97796b0342fd91fe73a614560637
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

Loading…