Triethylamine → (S)-benzyl 2-(1-(2-(3'-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate

HRID 333311노트

반응식

HRID 333311 반응식
[CH2:1]([O:8][C:9](=[O:19])[CH2:10][C:11]1([C:16]([OH:18])=O)[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20]CN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.C[C:50]1[CH:51]=[C:52]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH:53]=[CH:54][C:55]=1[CH2:56][C@@H:57]([C:59]1[NH:63][N:62]=[N:61][N:60]=1)[NH2:58]>CN(C=O)C.CCOC(C)=O>[CH3:20][C:68]1[CH:69]=[C:64]([C:52]2[CH:51]=[CH:50][C:55]([CH2:56][C@H:57]([NH:58][C:16]([C:11]3([CH2:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15]3)=[O:18])[C:59]3[NH:63][N:62]=[N:61][N:60]=3)=[CH:54][CH:53]=2)[CH:65]=[CH:66][CH:67]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acidHCID 178422619HCID 178422619, 화합물

생성물 1

HCID 178424508(S)-benzyl 2-(1-(2-(3'-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid (150 mg, 0.572 mmol) in DMF (3 mL) were added EDC-HCl (110 mg, 0.572 mmol), HOAt (62.3 mg, 0.423 mmol) and triethylamine (0.133 mL, 0.953 mmol) at room temperature. After being stirred for 0.5 hours, (S)-2-(3-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethanamine (106 mg, 0.381 mmol) was added and stirred for 2 hours. The reaction mixture was diluted with EtOAc and washed with saturated NH4Cl aqueous solution and brine. The organic layer was dried over Na2SO4, concentrated under reduced pressure, and purified by silica gel flash column chromatography (10% MeOH in DCM/DCM) to give (S)-benzyl 2-(1-(2-(3′-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate. LCMS (condition A): 524 (M+1); retention time=1.82 min.

후처리

  1. stirringstirred for 2 hours
  2. washwashed with saturated NH4Cl aqueous solution and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel flash column chromatography (10% MeOH in DCM/DCM)

출처 및 근거

ORD 기록
ord-f6c32a3a12634e04b4d04c56ace359bf
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877815B2

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