Phenylethanolamine → HCID 54400687, compound

HRID 1105621Notes

Reaction equation

[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][NH2:4].[C:11]([C:16]([CH3:28])=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](=O)[CH3:26])=[CH:20][CH:19]=1)([O:13][CH2:14][CH3:15])=[O:12]>>[C:11]([C:16]([CH3:28])=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:26])=[CH:20][CH:19]=1)([O:13][CH2:14][CH3:15])=[O:12]

Participants

Reactant 2

HCID 1000Phenylethanolamine

HCID 53707784HCID 53707784, compound

Product 1

HCID 54400687HCID 54400687, compound

Procedure

This was prepared in an identical manner to the compound described in Example 1 using 2-hydroxy-2-phenylethanamine (0.51 g) and 4-{2-carboethoxy-2-methylethenyl}phenylpropan-2-one (1.0 g). The title compound was isolated as an oil (1.4 g). The oil was dissolved in methanol and treated with fumaric acid (0.43 g) in methanol. Evaporation of the solvent gave an oil which was triturated with ethyl acetate and recrystallized from ethyl acetate to give the title compound hemifumarate (0.38 g) as a 50:50 mixture of diastereoisomers m.p. 135°-138° C. τ(CDCl3) 8.8 (3H, d, J=6 Hz), 8.7 (3H, t, J=7 Hz) 8.0 (3H, s), 6.35-7.5 (7H, m, 2H disappears with D2O), 5.8 (2H, q, J=7 Hz) 4.85 (1H, m), 3.15 (1H, s), 2.8 (9H, m), 2.47 (1H, s), 1.8 (2H, broad, disappears with D2O).

Workup

customThis was prepared in an identical manner to the compound

Sources & evidence

ORD record: ord-388fc1c1873344dab87ec9d2de3570b8
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04309443

Reaction notes

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