N-(Diphenylmethylene)glycine tert-butyl ester → 2-(Benzhydrylidene-amino)-3-cyclooctyl-propionic acid tert-butyl ester

HRID 1018851노트

반응식

HRID 1018851 반응식
[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[CH:31]1([CH2:39]I)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>O1CCCC1>[C:1]([O:5][C:6](=[O:22])[CH:7]([N:8]=[C:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:39][CH:31]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2724682Lithium diisopropylamideHCID 2763007Iodomethylcyclooctane

생성물 1

HCID 865854002-(Benzhydrylidene-amino)-3-cyclooctyl-propionic acid tert-butyl ester수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (Benzhydrylidene-amino)-acetic acid tert-butyl ester (3.00 g; 10.1 mmol) in 60 mL of tetrahydrofuran under argon at −78° C. was added lithium diisopropylamide solution (11.5 mL; 1.5 M solution in cyclohexane) dropwise. After 30 minutes, a solution of cycloheptylmethyl iodide (Prepared in Step A; 3.83 g; 15.2 mmol) was added dropwise via syringe and the mixture allowed to warm to room temperature and stirred for 18 h. The mixture was quenched with saturated sodium bicarbonate solution and most of the tetrahydrofuran was removed in vacuo. The mixture was diluted with water and extracted with methylene chloride. The combined extracts were dried (sodium sulfate) filtered and concentrated in vacuo. The crude product was chromatographed (eluent:4% ethyl acetate/hexanes) to give 3.34 g (79%) of 2-(Benzhydrylidene-amino)-3-cyclooctyl-propionic acid tert-butyl ester as a pale yellow oil.

후처리

  1. customThe mixture was quenched with saturated sodium bicarbonate solution and most of the tetrahydrofuran
  2. customwas removed in vacuo
  3. additionThe mixture was diluted with water
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined extracts were dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was chromatographed (eluent:4% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-795c2ea9cce34fc09b3dcd5acd6aec00
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482951B2

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