Diisopropylethylamine → N2-(tert-butoxycarbonyl)-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide

HRID 58330

반응식

HRID 58330 반응식
[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[BrH:34].[Br-].[CH3:36][NH:37][CH2:38][CH2:39][CH2:40][P+:41]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][C:10]([N:37]([CH3:36])[CH2:38][CH2:39][CH2:40][P+:41]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4].[Br-:34]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 19897074[3-(Methylamino)propyl]triphenylphosphonium Bromide Hydrobromide

생성물 1

HCID 131736995N2-(tert-butoxycarbonyl)-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide수율 77.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

N-(tert-butoxycarbonyl)-N-methylglycine (309 mg, 1.63 mmol) was taken up in methylene chloride (7.8 mL) and treated with N,N-diisopropylethylamine (1.0 mL, 5.7 mmol), and 1-hydroxybenzotriazole hydrate (233 mg, 1.52 mmol). After 10 minutes at room temperature, [3-(methylamino)propyl](triphenyl)phosphonium bromide hydrobromide (933 mg, 1.88 mmol) was added, followed by 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (353 mg, 1.84 mmol) and 4-dimethylaminopyridine (145 mg, 0.11 mmol). The mixture was stirred overnight at room temperature. The reaction was isolated by washing with aqueous NaHCO3 and water to give crude product that was purified on a silica gel column eluting with 5-10% 1 M NH3 in methanol and methylene chloride to give the title compound (739 mg) in a 76% yield.

후처리

  1. customThe reaction was isolated
  2. washby washing with aqueous NaHCO3 and water
  3. customto give crude product that
  4. customwas purified on a silica gel column
  5. washeluting with 5-10% 1 M NH3 in methanol and methylene chloride

출처 및 근거

ORD 기록
ord-5840f81b84034dd7b1d6e7d1e9abddf0
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434753B2

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