Dicyclohexylcarbodiimide → HCID 178426809、化合物

HRID 1886495ノート

反応式

HRID 1886495 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 178426809HCID 178426809、化合物収率 56.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-91266a0c68b34bc3b69449d566c1bdcf
出典データセット
uspto-grants-1992_09
特許番号
US05151497

反応ノート

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