1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (+/-)-2-Methyl-3-(methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

HRID 1024488노트

반응식

HRID 1024488 반응식
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([CH2:13][NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:3]=1.[CH3:19][CH:20]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])C)=[O:27])[C:21]([OH:23])=O.Cl.[CH2:34](N=C=NCCCN(C)C)C.CC1C=CN=C(N)C=1C>C(Cl)Cl>[CH3:19][CH:20]([CH2:24][NH:25][C:26]([O:28][CH:29]([CH3:31])[CH2:32][CH3:34])=[O:27])[C:21]([N:14]([CH2:13][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:23]

참가 물질

6

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 41926403-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acidHCID 110078842-Amino-3,4-dimethylpyridineHCID 43087680N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine

생성물 1

HCID 66726391(+/-)-2-Methyl-3-(methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The mixture of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine (600 mg), (±)-2-Methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid (200 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (475 mg) and of dimethyl aminopyridine (284 mg) in DCM (30 ml) was stirred overnight. The reaction mixture was partitioned between ethyl acetate and water (30 mL each). The aqueous layer was extracted with EtOAc (30 mL×2). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica (33% ethyl acetate in hexane) to give (±)-2-Methyl-3-(methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide as a resin: MS (m+1)=455.5.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water (30 mL each)
  2. extractionThe aqueous layer was extracted with EtOAc (30 mL×2)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica (33% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-2dec416a0723464784cfdb694c18d998
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722896B2

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