Sodium Hydroxide → HCID 68834969, compound

HRID 747762Notes

Reaction equation

HRID 747762 reaction equation
[C:1]1([S:7]([NH:10][C@@H:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])[CH2:26][CH2:25]3)=[CH:19][CH:18]=2)[C:12]([O:14]C)=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl.Cl.[NH2:44][C:45]1[CH:46]=[C:47]([CH:51]=[CH:52][CH:53]=1)[C:48]([NH2:50])=[NH:49].CCN=C=NCCCN(C)C>CO.O1CCCC1.N1C=CC=CC=1>[C:48]([C:47]1[CH:46]=[C:45]([NH:44][C:12](=[O:14])[C@@H:11]([NH:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[O:31])[CH2:26][CH2:25]3)=[CH:21][CH:22]=2)[CH:53]=[CH:52][CH:51]=1)(=[NH:49])[NH2:50]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 30846513-Aminobenzene-1-carboximidamide--hydrogen chloride (1/2)HCID 86760713HCID 86760713, compound

Product 1

HCID 68834969HCID 68834969, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1.75 g (3.26 mmol) of methyl (2S)-2-(benzenesulfonylamino)-3-[4-[1-(benzyloxycarbonyl)-4-piperidyloxy]phenyl]propionate was dissolved in a mixed solvent of 10 ml of methanol and 10 ml of tetrahydrofuran. 6.52 ml (6.52 mmol) of 1 N aqueous sodium hydroxide solution was added to the solution, and they were stirred at 50° C. overnight. The reaction mixture was washed with ether and then made acidic with concentrated hydrochloric acid. After the isolation process with dichloromethane as the extractant in the same manner as that of step 1 in Example 1, an oily residue was obtained, which was dissolved in 60 ml of pyridine. 747 mg (3.61 mmol) of 3-aminobenzamidine dihydrochloride and 750 mg (3.92 mmol) of WSC were added to the solution, and they were stirred at room temperature overnight. The solvent was distilled off, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. washThe reaction mixture was washed with ether
  2. customAfter the isolation process with dichloromethane as the extractant in the same manner as that of step 1 in Example 1, an oily residue was obtained
  3. stirringwere stirred at room temperature overnight
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-6bb77e3980b54f5da2b29454cb94931d
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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