2-Aminopropanol → 1-Bromocyclopropanecarboxylic acid-2-hydroxy-1-methylethylamide

Reaction equation

[OH:1][CH2:2][C@H:3]([NH:10][C:11]([C:13]1([Br:16])[CH2:15][CH2:14]1)=[O:12])[C:4]1C=CC=CC=1.BrC1(C(Cl)=O)CC1.CC(N)CO>>[OH:1][CH2:2][CH:3]([NH:10][C:11]([C:13]1([Br:16])[CH2:14][CH2:15]1)=[O:12])[CH3:4]

Participants

Reactant 3

HCID 51262-Aminopropanol

HCID 109102061-Bromocyclopropane-carboxylic acid chloride

HCID 21350875(IR)-1-bromocyclopropanecarboxylic acid-2-hydroxy-1-phenylethylamide

Product 1

HCID 180008511-Bromocyclopropanecarboxylic acid-2-hydroxy-1-methylethylamide

Procedure

Analogously to the production of amide 110, 2.18 g of acid chloride 107 is reacted with 780 mg of DL-2-amino-1-propanol, whereby 1.7 g of 1-bromocyclopropanecarboxylic acid-2-hydroxy-1-methylethylamide 112 is obtained as a colorless oil.

Sources & evidence

ORD record: ord-ccb6727b4be241dd9f32c6df90210cd0
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642218B2

Reaction notes

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