Dicyclohexylcarbodiimide → (+/-)-Phenylmethyl-[1-(hydroxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

HRID 327826

반응식

HRID 327826 반응식
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.C1CCC(N=C=NC2CCCCC2)CC1.[C:22]([NH:32][CH:33]([C:36](O)=[O:37])[CH2:34][OH:35])([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C(Cl)Cl>[C:26]1([CH2:25][O:24][C:22](=[O:23])[NH:32][CH:33]([CH2:36][OH:37])[C:34](=[O:35])[NH:1][N:2]2[CH:6]=[CH:5][CH:4]=[CH:3]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 76007N-carbobenzoxy-serineHCID 1365891-Aminopyrrole

생성물 1

HCID 23252862(+/-)-Phenylmethyl-[1-(hydroxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate수율 51.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-aminopyrrole (4.92 g) and DCC (6.18 g) in dry DCM (100 ml) was added carbobenzyloxy-D,L-serine (7.18 g) in small portions over a period of about 1 hour. After stirring overnight at room temperature, the precipitate was removed by filtration, and stirred in boiling ethyl acetate. The mixture was filtered and the filtrate was combined with the filtrate of the reaction mixture and evaporated to dryness. The residue was purified by flash column chromatography (silica gel, DCM/methanol 20:1) and the appropriate fractions were concentrated. Recrystallization of the residue from ethyl acetate afforded 4.68 g of the product as a powder, m.p. 153°-154° C.

후처리

  1. customthe precipitate was removed by filtration
  2. stirringstirred
  3. filtrationThe mixture was filtered
  4. customevaporated to dryness
  5. customThe residue was purified by flash column chromatography (silica gel, DCM/methanol 20:1)
  6. concentrationthe appropriate fractions were concentrated
  7. customRecrystallization of the residue from ethyl acetate

출처 및 근거

ORD 기록
ord-a8bb5211b91e4979b07b087b303ead55
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274116

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