Glyoxal, phenyl-, hydrate → N-{3-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)-1, 1-dimethylpropyl}-2-hydroxy-2-phenylethanamine

HRID 1105626Notes

Reaction equation

HRID 1105626 reaction equation
O.[C:2]1([C:8]([CH:10]=O)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([CH:16]=[C:17]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([CH3:30])([CH3:29])[NH2:28])=[CH:21][CH:20]=1)[CH3:18])([O:14][CH3:15])=[O:13]>>[C:12]([CH:16]=[C:17]([C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][C:27]([NH:28][CH2:10][CH:8]([OH:9])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([CH3:30])[CH3:29])=[CH:23][CH:24]=1)[CH3:18])([O:14][CH3:15])=[O:13]

Participants

3

Reactant 2

HCID 12215922Glyoxal, phenyl-, hydrateHCID 54395225HCID 54395225, compound

Product 1

HCID 53809482N-{3-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)-1, 1-dimethylpropyl}-2-hydroxy-2-phenylethanamineYield 64.6%

Procedure

This was prepared in an identical manner to the compound described in Example 13 using phenylglyoxal monohydrate (1.34 g) and 3-{4-(2-carbomethoxy-1-methylethenyl)phenyl}-1, 1-dimethylpropanamine (2.61 g). The title compound (2.17 g) m.p. 98°-102° C. (benzene-hexane) was obtained after chromatography on Kieselgel 60 eluting with 1% methanolchloroform. τ(CDCl3) 8.85 (6H, s), 8.1-8.7 (2H, m), 6.8-7.8 (9H, m), 6.2 (3H, s), 5.3 (1H, dd), 3.82 (1H broad), 2.65 (9H, m).

Workup

  1. customThis was prepared in an identical manner to the compound

Sources & evidence

ORD record
ord-8049c9d0d0174423b29f52be81180416
Source dataset
uspto-grants-1982_01
Patent number
US04309443

Reaction notes

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