Acetic Acid → HCID 86753680, compound

HRID 361766Notes

Reaction equation

HRID 361766 reaction equation
[N:1]1([C:7]([C:9]2[CH:37]=[CH:36][C:12]([C:13]([NH:15][CH:16]([CH2:34][CH3:35])[C:17]([CH3:33])([CH3:32])[C:18]([N:20]3[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([O:29]CC)=[O:28])[CH2:22][CH2:21]3)=[O:19])=[O:14])=[CH:11][CH:10]=2)=[NH:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].C(O)(=O)C>C(O)C>[N:1]1([C:7]([C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:15][CH:16]([CH2:34][CH3:35])[C:17]([CH3:32])([CH3:33])[C:18]([N:20]3[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([OH:29])=[O:28])[CH2:22][CH2:21]3)=[O:19])=[O:14])=[CH:36][CH:37]=2)=[NH:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86753679HCID 86753679, compound

Product 1

HCID 86753680HCID 86753680, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-(N-(4-(4-morpholinoimidoyl)benzoyl)-β-ethyl-α,α-dimethyl-β-alanyl)-4-piperidineacetate (28 mg, 54.4 mmol) as prepared in Example 43 was dissolved in ethanol (10 ml). To the resulting solution was added a 4N aqueous solution of NaOH (3 ml) under cooling with ice and the mixture was stirred for 3 hours. The mixture was neutralized with acetic acid under cooling with ice. After the ethanol was distilled off, the residue was dissolved in water and purified with a high performance liquid chromatography (HPLC) [column: ODS 5C18 (μ bondasphere, φ 19×150 mm), mobile phase: (A) 0.1% TFA, (B) 100% CH3CN/0.1% TFA, gradient: (A):(B)=76:24-74:26, 6 minutes, flow rate: 17 ml/min]. The desired fractions were collected and lyophilized to yield the titled compound (20.3 mg, 77%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. distillationAfter the ethanol was distilled off
  4. dissolutionthe residue was dissolved in water
  5. custompurified with a high performance liquid chromatography (HPLC) [column: ODS 5C18 (μ bondasphere, φ 19×150 mm), mobile phase: (A) 0.1% TFA, (B) 100% CH3CN/0.1% TFA, gradient: (A):(B)=76:24-74:26, 6 minutes, flow rate: 17 ml/min]
  6. customThe desired fractions were collected

Sources & evidence

ORD record
ord-fffe55db1ab8493fa5a5e247dcba2841
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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