Ethanolamine → HCID 21189863, compound

HRID 1068585Notes

Reaction equation

[Br:1][CH2:2][CH2:3][C:4]1[O:5][CH2:6][CH2:7][N:8]=1.BrCCC(O)=[O:13].C1N=CN(C(N2C=NC=C2)=O)C=1.C(CN)O>>[OH:5][CH2:6][CH2:7][NH:8][C:4](=[O:13])[CH2:3][CH2:2][Br:1]

Participants

Reactant 4

HCID 700Ethanolamine

HCID 115533-Bromopropionic acid

HCID 682631,1'-Carbonyldiimidazole

HCID 14093516HCID 14093516, compound

Product 1

HCID 21189863HCID 21189863, compound

Procedure

The required intermediate, 2-(2-bromoethyl)oxazoline, is prepared in a two-step process starting with 3-bromopropionic acid. Reaction of this acid with CDI followed by ethanolamine gives N-(2-hydroxyethyl)-3-bromopropionamide. Treatment of this compound with triphenylphosphine (PPh3) and DEAD in THF yields 2-(2-bromoethyl)oxazoline.

Sources & evidence

ORD record: ord-249412554cb34db382cd496cbb835fa0
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251898B1

Reaction notes

Loading…