Triethylamine → (R)-1-(4-chlorobenzyl)-3-[[N-(4-dimethylaminobenzoyl)glycyl]amino]pyrrolidine

HRID 1280949

반응식

HRID 1280949 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][C:13](=[O:16])[CH2:14][NH2:15])[CH2:8]2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:26][N:27]([CH3:37])[C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][C:13](=[O:16])[CH2:14][NH:15][C:32](=[O:33])[C:31]3[CH:30]=[CH:29][C:28]([N:27]([CH3:26])[CH3:37])=[CH:36][CH:35]=3)[CH2:8]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 120924-(Dimethylamino)benzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 54551710(R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine

생성물 1

HCID 69215736(R)-1-(4-chlorobenzyl)-3-[[N-(4-dimethylaminobenzoyl)glycyl]amino]pyrrolidine

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of (R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine (13.8 mg, 0.052 mmol) in CHCl3 (2 mL) was treated with Et3N (0.021 mL, 0.15 mmol), 4-(dimethylamino)benzoic acid (10 mg, 0.061 mmol), EDCI (10.2 mg, 0.053 mmol) and HOBt (7.5 mg, 0.055 mmol). The reaction mixture was stirred at room temperature for 16 h. The solution was washed with 2 N aqueous NaOH solution (2 mL×2) and brine (2 mL), and dried by filtration through a PTFE membrane using CH2Cl2 (3 mL). Concentration afforded the desired material (compound No. 952) (24.9 mg, quant): The purity was determined by RPLC/MS (91%); ESI/MS m/e 415.0 (M++H, C22H27ClN4O2).

후처리

  1. washThe solution was washed with 2 N aqueous NaOH solution (2 mL×2) and brine (2 mL)
  2. dry with materialdried by filtration through a PTFE membrane
  3. concentrationConcentration

출처 및 근거

ORD 기록
ord-c1216aed88664c66a1c17263040677a0
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451842B1

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