Methyl 4-(2-aminoethyl)benzoate → N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-(4-benzyloxy-3-nitrophenyl)-2-hydroxyethanamine

HRID 580625Notes

Reaction equation

HRID 580625 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH:17]=O)=[O:16])=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C=CC(CCN)=CC=1)(OC)=O.[C:35]([C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH:46]([CH3:48])[NH2:47])=[CH:41][CH:40]=1)([O:37][CH3:38])=[O:36]>>[C:35]([C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH:46]([NH:47][CH2:17][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]([N+:19]([O-:21])=[O:20])[CH:11]=2)[OH:16])[CH3:48])=[CH:41][CH:40]=1)([O:37][CH3:38])=[O:36]

Participants

4

Reactant 3

HCID 11183521Methyl 4-(2-aminoethyl)benzoateHCID 15034329Methyl 4-(2-aminopropyl)benzoateHCID 201341724-Benzyloxy-3-nitrophenyl glyoxal

Product 1

HCID 20134229N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-(4-benzyloxy-3-nitrophenyl)-2-hydroxyethanamine

Procedure

The title compound was prepared as a mixture of diastereoisomers by the process of Example 25, replacing phenyl glyoxal by 4-benzyloxy-3-nitrophenyl glyoxal and 2-(4-carbomethoxyphenyl)ethanamine by 2-(4-carbomethoxyphenyl)-1-methylethanamine. τ (CDCl3) 8.93 (3H, d, J=6 Hz), 6.70-7.80 (7H, m), 6.14 (3H, s), 5.40 (1H, m), 4.81 (2H, s) 2.30-3.10 (10H, m), 2.02 (2H, d, J=8 Hz).

Sources & evidence

ORD record
ord-54d32f90019b44fea62853caf2b56b16
Source dataset
uspto-grants-1988_06
Patent number
US04753962

Reaction notes

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