Dicyclohexylcarbodiimide → N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteinyl-L-proline tert-butyl ester

HRID 262784ノート

反応式

HRID 262784 の反応式
[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:38]([O:42][C:43]([NH:45][C@@H:46]([C:58](O)=[O:59])[CH2:47][S:48][CH2:49][C:50]1[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=1)=[O:44])([CH3:41])([CH3:40])[CH3:39]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:58](=[O:59])[C@@H:46]([CH2:47][S:48][CH2:49][C:50]1[CH:51]=[CH:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=1)[NH:45][C:43]([O:42][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:44])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 6992555N-[(1,1-Dimethylethoxy)carbonyl]-S-[(4-methoxyphenyl)methyl]-D-cysteineHCID 178418300HCID 178418300、化合物

生成物 1

HCID 22805345N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteinyl-L-proline tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of L-proline tert-butyl ester (0.85 g) and hydroxybenzotriazole (0.67 g) in methylene chloride (10 ml) chilled in an ice bath, dicyclohexylcarbodiimide (1.03 g) and N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteine (1.7 g) are added in that order. After fifteen minutes, the ice bath is removed and the mixture is stirred at room temperature overnight. The precipitate is filtered off and the filtrate is washed with 10% potassium bisulfate, water, saturated sodium bicarbonate, and water. The organic phase is dried and concentrated to dryness in vacuo to give N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteinyl-L-proline tert-butyl ester as an oil. Rf =0.2 (silica gel, chloroform).

後処理

  1. waitAfter fifteen minutes
  2. customthe ice bath is removed
  3. filtrationThe precipitate is filtered off
  4. washthe filtrate is washed with 10% potassium bisulfate, water, saturated sodium bicarbonate, and water
  5. customThe organic phase is dried
  6. concentrationconcentrated to dryness in vacuo

出典と根拠

ORDレコード
ord-55cc8e38b07944aea1844e2ea659f99e
出典データセット
uspto-grants-1979_05
特許番号
US04154946

反応ノート

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