Diisopropylcarbodiimide → HCID 54181953, Verbindung

HRID 613216

Reaktionsgleichung

Reaktionsgleichung von HRID 613216
[C:1]([O:5][C:6]([N:8]([CH2:43][C:44]([S:47][C:48]([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([CH3:46])[CH3:45])[CH2:9][CH2:10][N:11]([CH2:19][C:20]([CH3:42])([S:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:21])[CH2:12][CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:70]=C=NC(C)C)(C)C.ON1C(=O)CCC1=O.NCCN(CCN)CCN>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH2:43][C:44]([S:47][C:48]([C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)([CH3:45])[CH3:46])[CH2:9][CH2:10][N:11]([CH2:19][C:20]([CH3:42])([S:22][C:23]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH3:21])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH2:70])=[O:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 12734DiisopropylcarbodiimideHCID 77731Tris(2-aminoethyl)amineHCID 80170N-HydroxysuccinimideHCID 53724287HCID 53724287, Verbindung

Produkt 1

HCID 54181953HCID 54181953, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

BAT-BM was prepared as follows. BAT acid (N9 -(t-butoxycarbonyl)-N6,N9 -bis(2-methyl-2-triphenylmethylthiopropyl)-6,9-diazanonanoic acid) (10.03 g, 10.89 mmol) and 75 mL of dry methylene chloride (CH2Cl2) were added to a 250 mL round-bottomed flask equipped with magnetic stir bar and argon balloon. To this solution was added diisopropylcarbodiimide (3.40 mL, 21.7 mmol, 199 mole %), followed by N-hydroxysuccinimide (3.12g, 27.1 mmol, 249 mole %). This solution was observed to become cloudy within 1 h, and was further incubated with stirring for a total of 4 h at room temperature. A solution of tris(2-aminoethyl)amine (30 mL, 200 mmol, 1840 mole %) in 30 mL methylene chloride was then added and stirring continued overnight. The reaction mixture was then concentrated under reduced pressure, and the residue partitioned between ethylacetate (150 mL) and 0.5M potassium carbonate (K2CO3 ; 150 mL). The organic layer was separated, washed with brine and concentrated to give the crude product N-[2-N',N'-bis(2-aminoethyl)aminoethyl)]-N9 -(t-butoxycarbonyl)-N6,N9 -bis(2-methyl-2-triphenylmethylthiopropyl)-6,9-diazanonanamide as a foam/oil.

Aufarbeitung

  1. customBAT-BM was prepared
  2. customequipped with magnetic stir bar
  3. customwithin 1 h
  4. stirringstirring continued overnight
  5. concentrationThe reaction mixture was then concentrated under reduced pressure
  6. customthe residue partitioned between ethylacetate (150 mL) and 0.5M potassium carbonate (K2CO3 ; 150 mL)
  7. customThe organic layer was separated
  8. washwashed with brine
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4ab80fdf31b048899b5e73bf88efd563
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06007792

Verknüpfte Notizen

Wird geladen…