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

HRID 58330

Reaktionsgleichung

Reaktionsgleichung von HRID 58330
[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]

Komponenten

8

Edukt 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

Produkt 1

HCID 131736995N2-(tert-butoxycarbonyl)-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromideAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5840f81b84034dd7b1d6e7d1e9abddf0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434753B2

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