Ethanolamine → HCID 24992760, compound

HRID 1673217Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[O:14][C:15]([CH3:22])([CH3:21])[CH2:16][CH:17]([C:18](O)=[O:19])[C:11]2=[CH:10][C:9]=1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1.[CH2:30]([CH2:32][NH2:33])[OH:31]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[O:14][C:15]([CH3:22])([CH3:21])[CH2:16][CH:17]([C:18]([NH:33][CH2:32][CH2:30][OH:31])=[O:19])[C:11]2=[CH:10][C:9]=1[C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 700Ethanolamine

HCID 67020061HCID 67020061, compound

Product 1

HCID 24992760HCID 24992760, compound

Procedure

Using the product of Step B and ethanolamine, along with the procedure described in Example 88, the title compound was afforded. Further separation on an AS chiral column, eluting with 7% EtOH/heptane, afforded the enantiomers: (LC-2) HPLC/MS (fast isomer on AS): 471.3 (M+1), 473.3 (M+3); Rt=3.13 min. (LC-2) HPLC/MS (slow isomer on AS): 471.3 (M+1), 473.3 (M+3); Rt=3.13 min.

Sources & evidence

ORD record: ord-a5860d2d339e4fecaeea1897f956cf35
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999107B2

Reaction notes

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