Hydrochloric Acid → HCID 67208776、化合物

HRID 333306ノート

反応式

HRID 333306 の反応式
[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

参加物

10

反応物 7

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

生成物 1

HCID 67208776HCID 67208776、化合物収率 32%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e10adcc5636d458695eb9539fabfa4e3
出典データセット
uspto-grants-2014_11
特許番号
US08877815B2

反応ノート

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