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4-Methylmorpholine → HCID 67114148, Verbindung

HRID 41918
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 41918
[CH:1]1([CH:7]([NH:30][C:31]([C:33]2[CH:38]=[N:37][CH:36]=[CH:35][N:34]=2)=[O:32])[C:8]([NH:10][CH:11]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:12]([N:14]2[CH:22]3[CH:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:16][CH:15]2[C:23](O)=[O:24])=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CN1CCOCC1.Cl.[CH2:80]([O:82][C:83](=[O:91])[CH:84]([OH:90])[CH:85]([NH2:89])[CH2:86][CH2:87][CH3:88])[CH3:81]>O.ClCCl.CN(C)C=O>[CH2:80]([O:82][C:83](=[O:91])[CH:84]([OH:90])[CH:85]([NH:89][C:23]([CH:15]1[CH2:16][CH:17]2[CH:22]([CH2:21][CH2:20][CH2:19][CH2:18]2)[N:14]1[C:12](=[O:13])[CH:11]([NH:10][C:8](=[O:9])[CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[NH:30][C:31]([C:33]1[CH:38]=[N:37][CH:36]=[CH:35][N:34]=1)=[O:32])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:86][CH2:87][CH3:88])[CH3:81]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 79724-Methylmorpholine2×HCID 2724699PyBOPHCID 684917401-(2-{2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-indole-2-carboxylic acidHCID 85806087Ethyl 3-amino-2-hydroxyhexanoate hydrochloride

Produkt 1

HCID 67114148HCID 67114148, Verbindung
Ausbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a dry flask charged with a 1:1 mixture of dichloromethane-dimethylformamide (100 ml) was placed 1-(2-{2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-indole-2-carboxylic acid 32a (2.0 g, 4.28 mmols), PyBOP (2.5 g, 4.7 mmol), and N-methyl-morpholine (2.4 ml, 21.4 mmol) and the reaction placed under an atmosphere of nitrogen. In a 100 mL addition funnel was placed a solution of the amine 14(1.0 g, 4.7 mmols) and N-methyl-morpholine (0.60 ml, 5.35 mmol) in a 1:1 mixture of dichloromethane-dimethylformamide (10 ml). The reaction was cooled to 0° C., and the amine was added while maintaining the temperature at 0° C. The reaction was allowed to warm to ambient temperature as it was stirred over night. HPLC analysis showed the reaction to be complete, and then the reaction was diluted with water to 500 mL. After stirring the precipitate was filtered and dried to give 2.4 g (82% yield) of 32 as a beige solid. This material was used as is in the next step without further purification. HPLC: RT=5.66 min, (10-90% acetonitrile-water over 7 minutes); LC/MS: retention time 3.94 min (10-90% acetonitrile-water over 5 minutes); M+H+=685.5.

Aufarbeitung

  1. additionIn a 100 mL addition funnel
  2. temperaturewhile maintaining the temperature at 0° C
  3. temperatureto warm to ambient temperature as it
  4. customthe reaction
  5. stirringAfter stirring the precipitate
  6. filtrationwas filtered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e6009ce13687449ebf31cfe81f1476e0
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08536136B2

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