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

HRID 333311ノート

反応式

HRID 333311 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f6c32a3a12634e04b4d04c56ace359bf
出典データセット
uspto-grants-2014_11
特許番号
US08877815B2

反応ノート

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