Sodium Hydroxide → HCID 70074887, compound

HRID 1738721Notes

Reaction equation

HRID 1738721 reaction equation
[ClH:1].Cl.[C:3]([C:6]1[CH:31]=[CH:30][C:9]2[S:10][C:11]([CH2:13][CH:14]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C@H:25]4[CH2:29][CH2:28][NH:27][CH2:26]4)=[CH:20][CH:19]=3)[C:15]([OH:17])=[O:16])=[CH:12][C:8]=2[CH:7]=1)(=[NH:5])[NH2:4].Cl.[CH3:33][N:34]=[C:35](OCC)[CH3:36].[OH-].[Na+]>O.C(#N)C>[ClH:1].[ClH:1].[C:3]([C:6]1[CH:31]=[CH:30][C:9]2[S:10][C:11]([CH2:13][CH:14]([C:18]3[CH:19]=[CH:20][C:21]([O:24][C@H:25]4[CH2:29][CH2:28][N:27]([C:35](=[N:34][CH3:33])[CH3:36])[CH2:26]4)=[CH:22][CH:23]=3)[C:15]([OH:17])=[O:16])=[CH:12][C:8]=2[CH:7]=1)(=[NH:4])[NH2:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 22131001HCID 22131001, compoundHCID 70076132HCID 70076132, compound

Product 1

HCID 70074887HCID 70074887, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2.0 g of 3-(5-amidinobenzo[b]thien-2-yl)-2-[4-[((3S)-3-pyrrolidinyl)oxy]phenyl]propionic acid dihydrochloride was dissolved in a solvent mixture of 10 ml of water and 10 ml of acetonitrile. With stirring, to the thus prepared solution was gradually added 20 g of ethyl (N-methyl)acetimidate hydrochloride which has been prepared in accordance with the procedure disclosed in The Journal of Organic Chemistry (vol. 33, pp. 1679-1681, 1968), while maintaining the pH level of the solution at 8.5 with 2 N sodium hydroxide aqueous solution. After distilling off the solvent, the resulting residue was washed with dichloromethane and then subjected to column chromatography using a column packed with a highly porous polymer type synthetic adsorbent (styrene-divinylbenzene polymer: Diaion HP-20) and using a water/acetonitrile mixture as an elution solvent, thereby effecting desalting. Fractions of interest thus pooled were subjected to reversed phase high performance liquid chromatography using a column packed with octadecyl-bonded silica gel. Thereafter, the thus eluted fractions of interest were pooled and then concentrated to dryness by passing through a C1 type of strongly basic ion exchange resin (Diaion SA-10, Nippon Rensui Co., Ltd.). In this way, 370 mg of the title compound was obtained in a solid form.

Workup

  1. customhas been prepared in accordance with the procedure
  2. distillationAfter distilling off the solvent
  3. washthe resulting residue was washed with dichloromethane
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cf74a59179de4e468bae2c43d364b3ab
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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