1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Cbz-Asp(OBut)-Gly-OBn

HRID 964491

反応式

HRID 964491 の反応式
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].Cl.[NH2:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>ClCl.C(Cl)Cl>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([NH:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[O:13])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 11701227Benzyl 2-aminoacetate hydrochloride

生成物 1

HCID 14375963Cbz-Asp(OBut)-Gly-OBn収率 108.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24526Chlorine溶媒

実験手順

A mixture of Cbz-Asp(OBut)-OH (3590 mg, 11.1 mmol), HCl+H-Gly-OBn (3360 mg, 16.6 mmol), EDCI (3180 mg, 16.6 mmol), HOBt (2250 mg, 16.6 mmol) and DIEA (2900 mg, 16.6 mmol) in dry CH2 Cl2 (50 mL) was stirred at r.t. for six hours. The reaction mixture was added CH2Cl2 (150 mL) and washed with 1N HCl (200 mL), saturated NaHCO3 aq. (200 mL) and brine (200 mL). The organic layer was passed through an inch of SiO2 layer and the SiO2 was washed with 1/9=AcOEt/CH2Cl2 (200 mL). The eluent was evaporated in vacuo to give clear oil (5690 mg, 100%): 1H NMR (300 MHz, CDCl3) δ 7.368 (s, 10H), 7.082 (t, 1H), 6.013 (d, J=7.8 Hz, 1H), 5.164 (s, 2H), 5.126 (s, 2H), 4.592 (d, J=6.6 Hz, 1H), 4.072 (d, J=5.7 Hz, 2H), 2.891 (dd, J=18.2, 4.5 Hz, 1H), 2.641 (dd, J=17.1, 6.3 Hz, 1H), 1.423 (s, 9H); 13C NMR (300 MHz, CDCl3) δ 171.0, 170.9, 169.3, 136.1, 135.2, 129.7, 128.6 (2C), 128.4, 128.3, 128.2, 81.9, 67.3, 67.2, 51.1, 41.5, 37.3, 28.0.

後処理

  1. washwashed with 1N HCl (200 mL), saturated NaHCO3 aq. (200 mL) and brine (200 mL)
  2. washthe SiO2 was washed with 1/9=AcOEt/CH2Cl2 (200 mL)
  3. customThe eluent was evaporated in vacuo

出典と根拠

ORDレコード
ord-874846bbe82a4e449dc38c8d22cfa6f1
出典データセット
uspto-grants-1998_06
特許番号
US05770380

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