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

HRID 1988200노트

반응식

HRID 1988200 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
130 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-50f3d47aecef4d5daf2c5a09327fa2da
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553973B2

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