Lithium hydroxide, monohydrate → 3-(3,4-Diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid

HRID 644301Notes

Reaction equation

HRID 644301 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH:17][C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:32][CH2:31][C:30]4[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=4[NH:28][C:27]3=[O:37])[CH2:22][CH2:21]2)=[O:19])[C:13]([O:15]C)=[O:14])[CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH3:2].O.[OH-].[Li+]>CCO>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH:17][C:18]([N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[CH2:32][CH2:31][C:30]4[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=4[NH:28][C:27]3=[O:37])[CH2:24][CH2:25]2)=[O:19])[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22184617Methyl 3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionate

Product 1

HCID 221845783-(3,4-Diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

26 g of the crude product described in 3d) were dissolved in 200 mL EtOH, combined with 2.3 g (55 mmol) of lithium hydroxide hydrate and stirred overnight at RT. The reaction solution was concentrated by evaporation in vacuo, the residue was taken up with water, extracted with diethyl ether, acidified with citric acid solution and exhaustively extracted with EtOAc. The combined organic phases were dried over MgSO4 and evaporated down in vacuo.

Workup

  1. concentrationThe reaction solution was concentrated by evaporation in vacuo
  2. extractionextracted with diethyl ether
  3. extractionexhaustively extracted with EtOAc
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. customevaporated down in vacuo

Sources & evidence

ORD record
ord-0b404fcbc2144f2c9609e5df2725c7c3
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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