Dicyclohexylcarbodiimide → (S)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

HRID 22380

반응식

HRID 22380 반응식
[C:1]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH2:17][N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:5]1([CH2:4][O:3][C:1](=[O:2])[NH:11][C@@H:12]([CH3:13])[C:14](=[O:16])[NH:17][N:18]2[CH:22]=[CH:21][CH:20]=[CH:19]2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 1365891-AminopyrroleHCID 736104N-carbobenzyloxyalanine

생성물 1

HCID 15838188(S)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate수율 81.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of carbobenzyloxy-L-alanine (10.0 g) and N-aminopyrrole (3.68 g) in dry DCM (224 ml) was added DCC (9.71 g) at 0° C. under nitrogen. The cooling bath was removed after ten minutes and the reaction mixture was allowed to stir at room temperature for 17 hours. The mixture was filtered and the solid DCU filter cake was washed with hot ethyl acetate. Concentration of the combined filtrate gave the crude product. Recrystallization from ethyl acetate/hexane afforded 10.46 g of the product as a solid, m.p. 169°-171° C.

후처리

  1. customThe cooling bath was removed after ten minutes
  2. filtrationThe mixture was filtered
  3. filtrationthe solid DCU filter cake
  4. washwas washed with hot ethyl acetate
  5. customConcentration of the combined filtrate gave the crude product
  6. customRecrystallization from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-db24663bf31b482a858d169325ba9915
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428053

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