p-Toluenesulfonic acid → 3-[[(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester

HRID 1195136ノート

反応式

HRID 1195136 の反応式
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(O)(C1C=CC(C)=CC=1)(=O)=O.[NH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].C1CCC(N=C=NC2CCCCC2)CC1>ClC(Cl)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 1116164Benzyl 3-aminopropanoate

生成物 1

HCID 136862023-[[(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester収率 98%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

2.03 g of TEA was added to a mixture of 5.84 g of Boc-Phe-OH and 7.03 g of TosOH.β-Ala-OBzl in 80 ml of dichloroethane. 4.54 g of DCC was added to the solution at 0 ° C. After stirring for 3 hrs at 0 ° C. and overnight at room temperature, precipitated DCUrea was filtered off and the solvent was distilled in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with 10% citric acid aqueous solution, water, 5% sodium hydrogencarbonate aqueous solution and brine. After dehydration over sodium sulfate anhydride, the solvent was evaporated to give 8.36 g of Boc-Phe-β-Ala-OBzl; yield 98%.

後処理

  1. customprecipitated DCUrea
  2. filtrationwas filtered off
  3. distillationthe solvent was distilled in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with 10% citric acid aqueous solution, water, 5% sodium hydrogencarbonate aqueous solution and brine
  6. customAfter dehydration over sodium sulfate anhydride, the solvent was evaporated

出典と根拠

ORDレコード
ord-3a2a66bb0c7544188992b04270ad5310
出典データセット
uspto-grants-1992_05
特許番号
US05110797

反応ノート

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