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

HRID 333311Notes

Reaction equation

HRID 333311 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f6c32a3a12634e04b4d04c56ace359bf
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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