Triethylamine → HCID 86665067, compound

HRID 333312Notes

Reaction equation

HRID 333312 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.[NH2:20][C@@H:21]([C:35]1[N:39]([CH2:40][CH2:41][C:42]#[N:43])[N:38]=[N:37][N:36]=1)[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[C:26]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:25]=[CH:24][C:23]([CH2:22][C@@H:21]([NH:20][C:16]([C:11]2([CH2:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15]2)=[O:18])[C:35]2[N:39]([CH2:40][CH2:41][C:42]#[N:43])[N:38]=[N:37][N:36]=2)=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acidHCID 68753516HCID 68753516, compound

Product 1

HCID 86665067HCID 86665067, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid (49.4 mg, 0.188 mmol) and (R)-3-(5-(1-amino-2-(biphenyl-4-yl)ethyl)-1H-tetrazol-1-yl)propanenitrile (50 mg, 0.157 mmol) in DMF (1.5 mL) were added EDC.HCl (36 mg, 0.188 mmol), HOAt (26 mg, 0.188 mmol) and triethylamine (0.033 mL, 0.236 mmol). After being stirred for 2 hours, the reaction mixture was diluted with EtOAc. The mixture was washed with H2O2O and brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel flash column chromatography (eluent; EtOAc/heptane) to give (R)-benzyl 2-(1-(2-(biphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate (39 mg). LCMS (condition A) δ 563 (M+1); retention time=1.85 min.

Workup

  1. washThe mixture was washed with H2O2O and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel flash column chromatography (eluent; EtOAc/heptane)

Sources & evidence

ORD record
ord-7894521324934f12a7a1d66cd91e2fc1
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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