Hydrochloric Acid → HCID 67208776, 화합물

HRID 333306노트

반응식

HRID 333306 반응식
[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

참가 물질

10

반응물 7

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

생성물 1

HCID 67208776HCID 67208776, 화합물수율 32%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e10adcc5636d458695eb9539fabfa4e3
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877815B2

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