Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro- → 4-[4-[2-[(4-amino-3,5-dichloro-beta-hydroxyphenethyl)amino]propyl]phenoxy]-3-hydroxy-1H-pyrrole-2,5-dione hemihydrate

HRID 465422Notes

Reaction equation

HRID 465422 reaction equation
[Na].[CH2:2]([C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[C:15](=[O:16])[NH:14][C:13](=[O:17])[C:12]=2[OH:18])=[CH:8][CH:7]=1)[C:3]([CH3:5])=[O:4].[NH2:21][C:22]1[C:27]([Cl:28])=[CH:26][C:25]([CH:29]([OH:32])[CH2:30][NH2:31])=[CH:24][C:23]=1[Cl:33].C([BH3-])#N.[Na+]>CO>[OH2:4].[NH2:21][C:22]1[C:23]([Cl:33])=[CH:24][C:25]([CH:29]([OH:32])[CH2:30][NH:31][CH:3]([CH3:5])[CH2:2][C:6]2[CH:20]=[CH:19][C:9]([O:10][C:11]3[C:15](=[O:16])[NH:14][C:13](=[O:17])[C:12]=3[OH:18])=[CH:8][CH:7]=2)=[CH:26][C:27]=1[Cl:28].[NH2:21][C:22]1[C:23]([Cl:33])=[CH:24][C:25]([CH:29]([OH:32])[CH2:30][NH:31][CH:3]([CH3:5])[CH2:2][C:6]2[CH:20]=[CH:19][C:9]([O:10][C:11]3[C:15](=[O:16])[NH:14][C:13](=[O:17])[C:12]=3[OH:18])=[CH:8][CH:7]=2)=[CH:26][C:27]=1[Cl:28]

Participants

6

Reactant 4

HCID 217242Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro-HCID 5003444Sodium cyanoborohydrideHCID 5360545SodiumHCID 547233674-(4-acetonylphenoxy)-3-hydroxy-1H-pyrrole-2,5-dione

Product 1

HCID 884742324-[4-[2-[(4-amino-3,5-dichloro-beta-hydroxyphenethyl)amino]propyl]phenoxy]-3-hydroxy-1H-pyrrole-2,5-dione hemihydrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the sodium salt of 4-(4-acetonylphenoxy)-3-hydroxy-1H-pyrrole-2,5-dione (1.41 g) and 2-(4-amino-3,5-dichlorophenyl)-2-hydroxy ethylamine (1.0 g) in methanol was treated with sodium cyanoborohydride (0.35 g) and stirred at ambient temperature for 18 hours. The solvent was removed in vacuo, the residue dissolved in acetone and purified by column chromatography on silica using acetone as eluent followed by methanol after the elution of fast-running impurities. The solid obtained was washed with acetone and filtered to give 4-[4-[2-[(4-amino-3,5-dichloro-β-hydroxyphenethyl)amino]propyl]phenoxy]-3-hydroxy-1H-pyrrole-2,5-dione hemihydrate as a (34:66) mixture of diastereoisomers.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in acetone
  3. custompurified by column chromatography on silica
  4. washafter the elution of fast-running impurities
  5. customThe solid obtained
  6. washwas washed with acetone
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7ebc169d52534cc09da67ca9d4c7f19b
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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