Tert-butoxycarbonylalanine → 4-[(S)-2-(tert-Butoxycarbonylamino)propionyl]aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyethyl)benzamide

HRID 2509

Reaction equation

HRID 2509 reaction equation
[NH2:1][CH2:2][C:3]1[CH:32]=[CH:31][C:6]([C:7]([N:9]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:11][O:12][CH3:13])=[O:8])=[CH:5][CH:4]=1.[C:33]([NH:40][C@H:41]([C:43](O)=[O:44])[CH3:42])([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].CCN=C=NCCCN(C)C.Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[C:36]([O:35][C:33]([NH:40][C@@H:41]([CH3:42])[C:43]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([C:22](=[O:30])[C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH2:20][CH2:21]2)[CH2:10][CH2:11][O:12][CH3:13])=[O:8])=[CH:31][CH:32]=1)=[O:44])=[O:34])([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 85082Tert-butoxycarbonylalanineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 196898584-Aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyethyl)benzamide

Product 1

HCID 678013884-[(S)-2-(tert-Butoxycarbonylamino)propionyl]aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyethyl)benzamideYield 72.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyethyl)benzamide (120 mg, 0.245 mmol) was dissolved in methylene chloride (5 ml) to which were subsequently added Boc-L-alanine (46.4 mg, 0.245 mmol) and EDC hydrochloride (52 mg, 0.270 mmol) while cooling in an ice bath. After 4 hours of stirring at the same temperature, the reaction solution was mixed with water (10 ml), adjusted to pH 8 with saturated sodium bicarbonate aqueous solution and then extracted with methylene chloride. Thereafter, the resulting organic layer was dried on anhydrous sodium carbonate, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate) to obtain 109 mg (68.9%) of the title compound in a colorless amorphous form.

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionextracted with methylene chloride
  3. dry with materialThereafter, the resulting organic layer was dried on anhydrous sodium carbonate
  4. customthe solvent was removed by evaporation
  5. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-455b69c6551746be8a9a9cf6a7695e89
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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