Dicyclohexylcarbodiimide → HCID 178426809, 화합물

HRID 1886495노트

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HRID 1886495 반응식
[CH3:1][C:2]1([CH3:11])[CH2:6][C:5](=[O:7])[CH2:4][CH:3]1[C:8]([OH:10])=O.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.Br.Br.[NH2:39][C@H:40]([C:47]([N:49]1[CH2:56][CH2:55][CH2:54][C@H:50]1[C:51]([NH2:53])=[O:52])=[O:48])[CH2:41][C:42]1[N:46]=[CH:45][NH:44][CH:43]=1>CN(C=O)C.C(N(CC)CC)C>[CH3:11][C:2]1([CH3:1])[CH2:6][C:5](=[O:7])[CH2:4][CH:3]1[C:8]([NH:39][C@H:40]([C:47]([N:49]1[CH2:56][CH2:55][CH2:54][C@H:50]1[C:51]([NH2:53])=[O:52])=[O:48])[CH2:41][C:42]1[N:46]=[CH:45][NH:44][CH:43]=1)=[O:10]

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 216436222,2-Dimethyl-4-oxocyclopentane-1-carboxylic acidHCID 178419276HCID 178419276, 화합물

생성물 1

HCID 178426809HCID 178426809, 화합물수율 56.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

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온도
0 °C

실험 절차

In DMF (2 ml) was dissolved 2,2 dimethyl-4-oxocyclopentanecarboxylic acid [W. H. Perkin, jun., J. F. Thorpe, J. Chem. Soc., 79, 729 (1901)] (100 mg), and HOBT (108 mg) was added to the solution, followed by addition of DCC (145 mg) under cooling at 0° C. The mixture was stirred at 5° C. over night. After addition of L-histidyl-L-prolinamide dihydrobromide (265 mg) followed by addition of triethylamine (0.134 ml), the mixture was stirred at 5° C. for 4 days. After the resultant precipitate was filtered off, the filtrate was concentrated under reduced pressure to dryness and the residue was subjected to silica gel column chromatography. The fractions eluted by chloroform:methanol:ammonia water (90:10:2) were combined and concentrated to dryness to give the title compound (140 mg) was obtained as powders.

후처리

  1. additionwas added to the solution
  2. stirringthe mixture was stirred at 5° C. for 4 days
  3. filtrationAfter the resultant precipitate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure to dryness
  5. washThe fractions eluted by chloroform:methanol:ammonia water (90:10:2)
  6. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-91266a0c68b34bc3b69449d566c1bdcf
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05151497

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