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

HRID 22386

반응식

HRID 22386 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 70832N-Cbz-d-alanineHCID 1365891-Aminopyrrole

생성물 1

HCID 131718294(R)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate수율 90.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution consisting of carbobenzyloxy-D-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 24 hours. The suspension was filtered and the DCU filter cake was washed with hot ethyl acetate. Concentration of the filtrate gave the crude product. Recrystallization from EtOAc/hexane afforded 11.69 g of the desired product as a solid, m.p. 172°-174° C.

후처리

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

출처 및 근거

ORD 기록
ord-2b203e932a2844f291e5a3f318da299c
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428053

연결된 노트

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