Dicyclohexylcarbodiimide → HCID 14010329, compound

HRID 2295104Notes

Reaction equation

HRID 2295104 reaction equation
[C:1]([O:9][C:10]1[CH:20]=[CH:19][C:13]([CH:14]([OH:18])[C:15]([OH:17])=O)=[CH:12][CH:11]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][CH:22]([NH2:39])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:26]=1.C1CCC(N=C=NC2CCCCC2)CC1>>[CH2:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH:14]([OH:18])[C:15](=[O:17])[NH:39][CH:22]([CH3:21])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:27][CH:26]=2)=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14010324HCID 14010324, compoundHCID 21472884HCID 21472884, compound

Product 1

HCID 14010329HCID 14010329, compound

Procedure

As pointed out above, a preferred embodiment of this invention employs a mixture of all four optical isomers of the compound of Example 7. This racemic mixture can be prepared by the method described above by reaction of dl-4-(benzoyloxy)mandelic acid with dl-1-methyl-3-(4-benzyloxyphenyl)propylamine in the presence of DCC to give racemic 1-(4-benzyloxyphenyl)-2-oxo-2-[1-methyl-3-(4-benzyloxyphenyl)propylamino]ethanol. Reduction of the latter compound and subsequent removal of the benzyl groups provides racemic 1-(4-hydroxyphenyl)-2-[1-methyl-3-(4-hydroxyphenyl)propylamino]-ethanol. This compound is more preferably prepared by the following procedure.

Workup

  1. customThis racemic mixture can be prepared by the method

Sources & evidence

ORD record
ord-56d379935ba54a599839fb5d51cac809
Source dataset
uspto-grants-1997_11
Patent number
US05691385

Reaction notes

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