Methanol → (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylic acid

HRID 270594노트

반응식

HRID 270594 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][C:11]([C:18]([OH:21])([CH3:20])[CH3:19])([C:14]([O:16]C)=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.O.O.[OH-].[Li+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][C:11]([C:18]([OH:21])([CH3:20])[CH3:19])([C:14]([OH:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86602446methyl (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylate

생성물 1

HCID 68596413(3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylic acid수율 49.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
110 °C

실험 절차

To a solution of methyl (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylate (1.0 g, 3.3 mmol) in a mixture of tetrahydrofuran (30 mL), methanol (30 mL) and water (6 mL) was added Lithium hydroxide monohydrate (0.22 g, 5.3 mmol) and the mixture refluxed overnight (110° C.). The organic solvents were evaporated and the aqueous layer was washed with ether one time. The aqueous layer was then acidified with 6 N HCl to about pH 4 and extracted with methylene chloride three times. The combined extracts were dried, filtered, and concentrated to provide the desired product (0.47 g, 49%).

후처리

  1. customThe organic solvents were evaporated
  2. washthe aqueous layer was washed with ether one time
  3. extractionextracted with methylene chloride three times
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-265e2743f9bd4aefa29d2d209b1b8b20
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449467B2

반응 노트

불러오는 중…