Cyanogen Bromide → 3-(5-Amino-1,3,4-oxadiazol-2-yl)pentan-3-ol

HRID 1988200ノート

反応式

HRID 1988200 の反応式
[CH2:1]([C:3]([OH:10])([CH2:8][CH3:9])[C:4](OC)=O)[CH3:2].[OH2:11].[NH2:12][NH2:13].Br[C:15]#[N:16]>O>[NH2:16][C:15]1[O:11][C:4]([C:3]([OH:10])([CH2:8][CH3:9])[CH2:1][CH3:2])=[N:13][N:12]=1

参加物

5

反応物 3

HCID 10476Cyanogen BromideHCID 24654Hydrazine hydrate (1:1)HCID 45037043Methyl 2-ethyl-2-hydroxybutanoate

生成物 1

HCID 574378393-(5-Amino-1,3,4-oxadiazol-2-yl)pentan-3-ol

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

A mixture of methyl 2-ethyl-2-hydroxybutanoate (19.7 g, 134.7 mol) and hydrazine hydrate (14 mL) was heated to 130° C. for 4 h. The mixture was cooled to rt and excess reagent removed under vacuum to yield of the hydrazide. To this hydrazide and KHCO3 (13.8 g, 138 mmol) in 150 mL of water was added portionwise BrCN (13.8 g, 131 mmol). After 90 min of stirring, the white solid was filtered, washed with ether and dried to yield the title compound. 1H NMR (400 MHz, acetone-d6): δ 6.20 (bs, 2H), 4.25 (s, 1H), 1.85 (m, 4H), 0.88 (t, 6H).

後処理

  1. temperatureThe mixture was cooled to rt
  2. customexcess reagent removed under vacuum to yield of the hydrazide
  3. filtrationthe white solid was filtered
  4. washwashed with ether
  5. customdried

出典と根拠

ORDレコード
ord-50f3d47aecef4d5daf2c5a09327fa2da
出典データセット
uspto-grants-2009_06
特許番号
US07553973B2

反応ノート

読み込み中…