1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 16122905, Verbindung

HRID 2264146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264146
[O:1]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1.C(O[C:23]([N:25]1[CH2:30][CH2:29][O:28][C@@H:27]([C:31]([OH:33])=O)[CH2:26]1)=O)(C)(C)C.O.ON1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.C(N(CC)CC)C>[CH2:23]([N:25]1[CH2:30][CH2:29][O:28][CH:27]([C:31]([N:13]([CH2:12][C:10]2[CH:9]=[CH:8][C:7]3[O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]=3[CH:11]=2)[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:33])[CH2:26]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Komponenten

7

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6559076(2R)-4-((tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 58080614N-((3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl)-2-methylpropan-1-amine

Produkt 1

HCID 16122905HCID 16122905, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 5.6 g of N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine, 5.0 g of (−)-(2R)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid, 0.8 g of 1-hydroxybenzotriazole hydrate and 5 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 3 mL of triethylamine in 100 mL in dichloromethane was stirred overnight. The mixture was concentrated under reduced pressure and partitioned between 100 mL of ethyl acetate and 100 mL of saturated sodium carbonate, dried over magnesium sulfate and concentrated under reduced pressure. Flash chromatography (20%-50% ethyl acetate/hexanes gradient elution) gave the product as a resin: MS (m+1)=449.3; H NMR (400 MHz, CDCl3) 7.3-6.7 (complex m, 5H), 4.6 (br d, 1H), 6.8-6.7 (m, 2H), 4.4 (d, 1H), 4.2 (m, 4H), 4.15 (q, 1H), 4.08 (br d, 1H), 3.95 (m, 1H), 3.5 (m, 1H), 3.2 (m, 1H), 3.0 (dd, 1H), 2.2 (m, 1H), 2.0 (m, 1H) 1.45 (2×s, 9H), 0.9 (dd, 6H).

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompartitioned between 100 mL of ethyl acetate and 100 mL of saturated sodium carbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washFlash chromatography (20%-50% ethyl acetate/hexanes gradient elution)
  6. customgave the product as a resin

Quellen und Nachweise

ORD-Eintrag
ord-f292eccdca77480e8c3cf73677d7f78d
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855201B2

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