HCID 73052642, 화합물 → HCID 69098014, 화합물

HRID 1503081노트

반응식

HRID 1503081 반응식
CON(C)[C:4]([CH2:6][C:7]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:9][CH2:8]1)=[O:5].[CH3:15][Li]>C1COCC1>[O:5]=[C:4]([CH3:15])[CH2:6][C:7]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:8][CH2:9]1

참가 물질

4

반응물 2

HCID 73052642HCID 73052642, 화합물HCID 178418348HCID 178418348, 화합물

생성물 1

HCID 69098014HCID 69098014, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3.6 g crude {1-[(methoxy-methyl-carbamoyl)-methyl]-cyclopropyl}-acetic acid (18 mmole) in 54 ml of THF are added 24.5 ml of methyllithium (1.6 M solution in diethyl ether, 39.2 mmole, 2.2 eq) at <−75° C. Stirring is continued for 2 hours, then the mixture is quenched by addition of 2 ml of methanol and warmed to room temperature. 54 ml of water are added and the phases are separated. The aqueous product phase is washed with 27 ml of methyl tert-butyl ether, acidified to pH 2.5 by addition of conc. HCl and extracted three times with 27 ml ethyl acetate each. The combined organic phases are concentrated to dryness and the residue is directly used in the next step (esterification to [1-(2-oxo-propyl)-cyclopropyl]-acetic acid methyl ester).

후처리

  1. customthe mixture is quenched by addition of 2 ml of methanol
  2. addition54 ml of water are added
  3. customthe phases are separated
  4. washThe aqueous product phase is washed with 27 ml of methyl tert-butyl ether
  5. additionacidified to pH 2.5 by addition of conc. HCl
  6. extractionextracted three times with 27 ml ethyl acetate each
  7. concentrationThe combined organic phases are concentrated to dryness

출처 및 근거

ORD 기록
ord-27fe9cdf95914b138e9851b3437845c4
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212120B2

반응 노트

불러오는 중…