Diisopropylethylamine → {(S)-2-Methyl-1-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butylcarbamoyl-]propyl}-carbamic acid tert-butyl ester

HRID 585875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585875
FC(F)(F)C([O-])=O.[CH3:8][CH:9]([CH3:26])[CH2:10][C@@H:11]([NH3+:25])[B:12]1[O:20][C@H:19]2[C@:14]([CH3:24])([C@H:15]3[CH2:21][C@@H:17]([CH2:18]2)[C:16]3([CH3:23])[CH3:22])[O:13]1.[C:27]([NH:34][C@H:35]([C:39](O)=[O:40])[CH:36]([CH3:38])[CH3:37])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:30]([O:29][C:27](=[O:28])[NH:34][C@H:35]([C:39](=[O:40])[NH:25][C@H:11]([B:12]1[O:20][C@H:19]2[C@:14]([CH3:24])([C@H:15]3[CH2:21][C@@H:17]([CH2:18]2)[C:16]3([CH3:23])[CH3:22])[O:13]1)[CH2:10][CH:9]([CH3:26])[CH3:8])[CH:36]([CH3:37])[CH3:38])([CH3:31])([CH3:33])[CH3:32]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 83693Boc-L-ValineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 20823732(S)-3-Methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butylammonium trifluoroacetate

Produkt 1

HCID 67492646{(S)-2-Methyl-1-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butylcarbamoyl-]propyl}-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The title compound is prepared as described in step B of example 1 but using (S)-3-Methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butylammonium trifluoroacetate ((C) in Synthetic Scheme 1) (for preparation see Kettner, C. A. and Shenvi, A. B. J. Biol. Chem. 1984, 259, p. 15106-15114 and Matteson, D. S. and Sadhu, K. M. J. Am. Chem. Soc. 1981, 103, p. 5241-5242) (2.395 g, 6.32 mMol), Boc-L-valine (1.373 g, 6.32 mMol), TBTU (2.23 g, 6.95 mMol, 1.1 equiv), DIEA (3.3 mL, 18.95 mMol, 3.0 equiv) and DMF (24 mL).

Aufarbeitung

  1. customfor preparation

Quellen und Nachweise

ORD-Eintrag
ord-e1b4bd628fe642e485f565b55d708c89
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933290B2

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