4-Methylmorpholine → N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-[(benzyloxycarbonyl)amino]-3-phenylpropyl}-D-alaninamide

HRID 1849988

Reaktionsgleichung

Reaktionsgleichung von HRID 1849988
[CH2:1]([O:8][C:9](=[O:26])[NH:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][NH:13][C:14](=[O:18])[C@@H:15]([CH3:17])[NH2:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][C:32]([NH:34][C@H:35]([C:46](O)=[O:47])[CH2:36][C:37]1[C:42]([CH3:43])=[CH:41][C:40]([OH:44])=[CH:39][C:38]=1[CH3:45])=[O:33])([CH3:30])([CH3:29])[CH3:28].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C.CCOC(C)=O>[C:27]([O:31][C:32]([NH:34][C@H:35]([C:46]([NH:16][C@@H:15]([C:14]([NH:13][CH2:12][C@H:11]([NH:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:26])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18])[CH3:17])=[O:47])[CH2:36][C:37]1[C:38]([CH3:45])=[CH:39][C:40]([OH:44])=[CH:41][C:42]=1[CH3:43])=[O:33])([CH3:29])([CH3:30])[CH3:28]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 13656657(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acidHCID 71229500HCID 71229500, Verbindung

Produkt 1

HCID 71212286N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-[(benzyloxycarbonyl)amino]-3-phenylpropyl}-D-alaninamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Benzyl-[(1R)-2-(D-alanylamino)-1-benzylethyl]carbamate (145 mg, 0.41 mmol) was combined with N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosine (described in BioOrg. Med. Chem. Letts, 2003, p 599; 129 mg, 0.41 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride salt (94 mg, 0.49 mmol), 1-hydroxybenzotriazole monohydrate (69 mg, 0.45 mmol) and N-methylmorpholine (42 mg, 0.41 mmol) in DMF (5 mL) at room temperature under a nitrogen atmosphere. The mixture was stirred at room temperature for 16 h and then diluted with 10 mL of EtOAc and washed with 10 mL of a 10% aqueous solution of citric acid, 10 mL of water, 10 mL of a 3% aqueous solution of sodium bicarbonate, and finally 10 mL of a saturated aqueous brine solution. The organic layer was dried over sodium sulfate and evaporated under reduced pressure to give 243 mg (92%) of a white foam of the title compound, which was used with no further purification.

Aufarbeitung

  1. washwashed with 10 mL of a 10% aqueous solution of citric acid, 10 mL of water, 10 mL of a 3% aqueous solution of sodium bicarbonate, and finally 10 mL of a saturated aqueous brine solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ae2bff5de7f74ea2bc643edf60046866
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957025B2

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