Lithium Hydroxide → HCID 86587230, compound

HRID 2414696Notes

Reaction equation

HRID 2414696 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([NH:26][CH2:27][C@H:28]([NH:32][C:33](=[O:44])[C:34]3[CH:39]=[CH:38][C:37]([C:40]([O:42]C)=[O:41])=[CH:36][CH:35]=3)[C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.[SiH3]CC(N)=O.CN1CCOCC1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>O>[NH:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([NH:26][CH2:27][C@H:28]([NH:32][C:33](=[O:44])[C:34]3[CH:35]=[CH:36][C:37]([C:40]([OH:42])=[O:41])=[CH:38][CH:39]=3)[C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:12][CH2:13]1

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 79724-MethylmorpholineHCID 516920Potassium bisulfateHCID 86587231HCID 86587231, compoundHCID 123643341HCID 123643341, compound

Product 1

HCID 86587230HCID 86587230, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-(4-methoxycarbonylbenzoyl)amino-β-alanine (55 mg, 0.106 mmol) in water (0.5 mL), monosilylacetamide (1.0 g) and N-methylmorpholine (61 mL, 0.55 mmol) was added 1N LiOH solution (0.37 mL) at 5° C. After stirring for 40 minutes, the mixture was neutralized with 20% aqueous KHSO4 solution, then purified by an ODS column chromatography using Daisogel-120sp (10% CH3CN/water) and freeze-dried to give N-[(R)-1-{3-(4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-(4-carboxybenzoyl)amino-β-alanine (40 mg, 75.1%) as a white powder.

Workup

  1. custompurified by an ODS column chromatography
  2. customfreeze-dried

Sources & evidence

ORD record
ord-54207647921c4dc39b32984a73228afc
Source dataset
uspto-grants-2004_11
Patent number
US06812235B2

Reaction notes

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