Diisopropylcarbodiimide → 3-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)pyrrolidine

HRID 279282

반응식

HRID 279282 반응식
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14](=[O:17])[CH2:15][NH2:16])[CH2:8]2)=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:22]=1[C:23](O)=[O:24].C(N=C=NC(C)C)(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)(Cl)Cl.C(O)(C)(C)C>[NH2:20][C:21]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:22]=1[C:23]([NH:16][CH2:15][C:14]([NH:13][CH2:12][CH:9]1[CH2:10][CH2:11][N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][CH:18]=2)[CH2:8]1)=[O:17])=[O:24]

참가 물질

7

반응물 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7359652-Amino-4,5-difluorobenzoic acidHCID 184262571-(4-Chlorobenzyl)-3-[(glycylamino)methyl]pyrrolidine

생성물 1

HCID 5088493-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)pyrrolidine

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6386tert-Butanol용매

실험 절차

A solution of 1-(4-chlorobenzyl)-3-{(glycylamino)methyl}pyrrolidine (0.050 mmol) in CHCl3 (1.35 mL) and tert-butanol (0.05 mL) was treated with 2-amino-4,5-difluorobenzoic acid (0.060 mmol), diisopropylcarbodiimide (0.060 mmol), and HOBt (0.060 mmol). The reaction mixture was stirred at room temperature for 19 h. The mixture was loaded onto Varian™ SCX column, and washed with CH3OH/CHCl3 1:1 (10 mL) and CH3OH (10 mL). Product was eluted off using 2 N NH3 in CH3OH (5 mL) and concentrated to afford 3-[{N-(2-amino-4,5-difluorobenzoyl)glycyl}aminomethyl]-1-(4-chlorobenzyl)pyrrolidine (Compound No. 1506) (22.0 mg, quant): The purity was determined by RPLC/MS (92%); ESI/MS m/e 437 (C21H23ClF2N4O2).

후처리

  1. washwashed with CH3OH/CHCl3 1:1 (10 mL) and CH3OH (10 mL)
  2. washProduct was eluted off
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-97d2064fc8cf446c8609e0045adfca72
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362177B1

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