1-Butanol → HCID 22876645, compound

HRID 1377529Notes

Reaction equation

HRID 1377529 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([CH2:12][C:13]([NH:15][C@H:16]([CH3:21])[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:8]2=[O:11])=[CH:4][CH:3]=1.Cl.Cl[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]Cl.CCO.O.[NH4+].[OH-].[CH2:36](O)[CH2:37][CH2:38][CH3:39]>>[CH2:36]([O:19][C:18](=[O:20])[CH2:17][C@@H:16]([CH3:21])[NH:15][C:13](=[O:14])[CH2:12][N:7]1[CH2:6][C:5]2[C:9](=[CH:10][C:2]([N:1]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:3][CH:4]=2)[C:8]1=[O:11])[CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 86596525Ethanol ammonium hydroxide waterHCID 86751223HCID 86751223, compound

Product 1

HCID 22876645HCID 22876645, compound

Procedure

N-{[6-Amino-2,3-dihydro-1(1H)-isoindolone-2-yl]acetyl}-(R)-methyl-β-alanine (2-7) (203 mg, 0.7 mmol) and bis(2-chloroethyl) amine hydrochloride (137 mg, 0.77 mmol) in n-butanol (10 mL) were heated at 110° C. for 3 days. The solvent was removed and the residue chromatographed OEtOH/H2O/NH4OH 10:0.5:0.5) to give 2-8. Rf (silica; EtOH/H2O/NH4OH 10:0.5:0.5)=0.61. ##STR62##

Workup

  1. customThe solvent was removed
  2. customthe residue chromatographed OEtOH/H2O/NH4OH 10:0.5:0.5)
  3. customto give 2-8

Sources & evidence

ORD record
ord-1e00e3d8d5bf4a09af1dfd63d99ebf66
Source dataset
uspto-grants-1997_09
Patent number
US05665723

Reaction notes

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