Guanidine Hydrochloride → HCID 178479507, compound

HRID 2299691Notes

Reaction equation

HRID 2299691 reaction equation
[ClH:1].[NH2:2][C:3]([NH2:5])=[NH:4].[O-]CC.[Na+].C([O:12][C:13](=O)[CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]2[CH2:25][CH2:24][CH2:23][CH:22]([NH:26][CH2:27][C@H:28]([OH:37])[CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:21][C:20]=2[CH:38]=1)C>CN(C)C=O>[ClH:1].[OH:37][C@H:28]([CH2:29][O:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:27][NH:26][CH:22]1[CH2:21][C:20]2[CH:38]=[C:16]([O:15][CH2:14][C:13]([NH:4][C:3]([NH2:5])=[NH:2])=[O:12])[CH:17]=[CH:18][C:19]=2[CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 2723922Sodium ethoxideHCID 69329972HCID 69329972, compound

Product 1

HCID 178479507HCID 178479507, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of guanidine hydrochloride (463 mg) in N,N-dimethylformamide (20 ml) was added 28% sodium ethoxide (0.22 ml) under ice-cooling, and the mixture was stirred at room temperature for 5 minutes. To the resulting mixture was added 2-[8-[(2S)-2-hydroxy-3-phenoxypropyl]amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetic acid ethyl ester (400 mg). After being stirred at room temperature for 2 hours, the precipitates were collected by filtration and treated with 4N hydrogen chloride in ethyl acetate to afford N-[2-[8-[(2S)-2-hydroxy-3-phenoxypropyl]amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetyl]guanidine hydrochloride (243 mg).

Workup

  1. temperaturecooling
  2. stirringAfter being stirred at room temperature for 2 hours
  3. filtrationthe precipitates were collected by filtration
  4. additiontreated with 4N hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-ac0ec094ae7b49b39dd295047b1efd95
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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