Hydrochloric Acid → HCID 67208776, compound

HRID 333306Notes

Reaction equation

HRID 333306 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([NH:17]C(OC(C)(C)C)=O)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:3][CH:2]=1.Cl.O1CCOCC1.[CH2:38]([O:45][C:46](=[O:56])[CH2:47][C:48]1([C:53](O)=[O:54])[CH2:52][CH2:51][CH2:50][CH2:49]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CCN=C=NCCCN(C)C.Cl.ON1C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:38]([O:45][C:46](=[O:56])[CH2:47][C:48]1([C:53]([NH:17][CH:8]([CH2:7][C:4]2[CH:5]=[CH:6][C:1]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:2][CH:3]=2)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11])=[O:54])[CH2:49][CH2:50][CH2:51][CH2:52]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59607675HCID 59607675, compoundHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid

Product 1

HCID 67208776HCID 67208776, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl 4-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)butanoate (110 mg, 0.267 mmol) and HCl in 1,4-dioxane (0.668 ml, 2.67 mmol) was stirred for 2 hours, and the reaction mixture was concentrated under reduced pressure. To a solution of 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid (65.6 mg, 0.214 mmol, 86% purity), EDC.HCl (51.2 mg, 0.267 mmol) and 1-hydroxy-7-azabenzotriazole (36.4 mg, 0.267 mmol) in DMF (1 ml) stirred for 1.5 hour, the obtained residue and DIPEA (0.093 ml, 0.535 mmol) were added. After stirred for 2.5 hours, the reaction was diluted with water. The products were extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 0:100) to give tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-4-(biphenyl-4-yl)butanoate (38 mg); Retention time=1.89 minutes (condition B); MS (m+1)=556.3.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. stirringAfter stirred for 2.5 hours
  3. extractionThe products were extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 0:100)

Sources & evidence

ORD record
ord-e10adcc5636d458695eb9539fabfa4e3
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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