1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-butyl L-prolinate

HRID 1176794노트

반응식

HRID 1176794 반응식
C1(C2C=CC=CC=2)C=CC(OCC2OC(C(O)=O)=CC=2)=CC=1.Cl.[C:24]([O:28][C:29](=[O:35])[C@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)([CH3:27])([CH3:26])[CH3:25].Cl.C(N=C=NCCCN(C)C)C>O1CCCC1>[C:24]([O:28][C:29]([CH:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)=[O:35])([CH3:27])([CH3:25])[CH3:26]

참가 물질

5

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 46831535-[(4-Phenylphenoxy)methyl]furan-2-carboxylic acid2회HCID 44629909tert-butyl (2R)-pyrrolidine-2-carboxylate hydrochloride

생성물 1

HCID 102884tert-butyl L-prolinate수율 61.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 5-(biphenyl-4-yloxymethyl)-furan-2-carboxylic acid (of Intermediate 8; 0.134 g, 0.46 mmol), D-proline tert-butyl ester hydrochloride (Bachem; 0.22 g, 1.1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (Avocado; 0.18 g, 0.95 mmol), and N,N-dimethylaminopyridine (0.166 g, 1.36 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 16 h. The solvents were evaporated under reduced pressure, and water and ethyl acetate were added. The aqueous phase was extracted three times with ethyl acetate, and the combined organic layers were dried (sodium sulfate), filtered, evaporated, and purified using a Biotage Flash 40 purification system, eluting with methylene chloride/acetone 9:1, to give 5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-D-pyrrolidine-2-carboxylic acid tert-butyl ester as a white solid (0.115 g, 56%).

후처리

  1. customThe solvents were evaporated under reduced pressure, and water and ethyl acetate
  2. additionwere added
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialthe combined organic layers were dried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. custompurified
  8. customa Biotage Flash 40 purification system
  9. washeluting with methylene chloride/acetone 9:1

출처 및 근거

ORD 기록
ord-aa46ff76b34a406d8723d471002ea434
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842825B2

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