1-Hydroxybenzotriazole → HCID 178520375, compound

HRID 333310Notes

Reaction equation

HRID 333310 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.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[Cl:42][C:43]1[CH:44]=[C:45]([C:49]2[CH:54]=[CH:53][C:52]([CH2:55][C@@H:56]([C:58]3[NH:62][N:61]=[N:60][N:59]=3)[NH2:57])=[CH:51][CH:50]=2)[CH:46]=[CH:47][CH:48]=1>C1COCC1>[Cl:42][C:43]1[CH:44]=[C:45]([C:49]2[CH:50]=[CH:51][C:52]([CH2:55][C@H:56]([NH:57][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:58]3[NH:62][N:61]=[N:60][N:59]=3)=[CH:53][CH:54]=2)[CH:46]=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acidHCID 178511761HCID 178511761, compound

Product 1

HCID 178520375HCID 178520375, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid (197 mg, 0.750 mmol) in THF (8 ml) at room temperature was added EDC.HCl (192 mg, 1.000 mmol) and HOBT (134 mg, 0.875 mmol). The mixture was stirred at room temperature for 10 minutes and was added a solution of (S)-2-(3′-chlorobiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethanamine (187 mg, 0.625 mmol) in THF and TEA (0.174 ml, 1.250 mmol). The mixture was stirred overnight at room temperature. The reaction was quenched by brine and was extracted with EtOAc. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, 1 to 3% EtOH/DCM) and gave the title compound: 134 mg (yield: 39%). LCMS (condition B): 544.3 (M+1); retention time=1.44 min.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe reaction was quenched by brine
  3. extractionwas extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by flash chromatography (silica gel, 1 to 3% EtOH/DCM)

Sources & evidence

ORD record
ord-e5a4dd9fbc59496a85eb71c484f5ca2f
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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