Diisopropylethylamine → (S)-4-tert-butoxycarbonylamino-4-(4-cyano-benzylcarbamoyl)-butyric acid benzyl ester

HRID 576548

Reaktionsgleichung

Reaktionsgleichung von HRID 576548
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:15]([OH:17])=O)[CH2:3][CH2:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.Cl.[NH2:62][CH2:63][C:64]1[CH:71]=[CH:70][C:67]([C:68]#[N:69])=[CH:66][CH:65]=1>CN(C=O)C.CCOC(C)=O>[CH2:7]([O:6][C:5](=[O:14])[CH2:4][CH2:3][C@H:2]([NH:1][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:15](=[O:17])[NH:69][CH2:68][C:67]1[CH:70]=[CH:71][C:64]([C:63]#[N:62])=[CH:65][CH:66]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 83589L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 5-(phenylmethyl) esterHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 99422504-(Aminomethyl)benzonitrile hydrochloride

Produkt 1

HCID 66994809(S)-4-tert-butoxycarbonylamino-4-(4-cyano-benzylcarbamoyl)-butyric acid benzyl esterAusbeute 106,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of Boc-Glu(OBzl)-OH (7.08 g, 21.0 mmol), BOP (9.72 g, 22.0 mmol) and DIEA (12.18 ml, 70.0 mmol) in DMF (50 ml) was maintained at room temperature for 20 min, followed by the addition of 4-(aminomethyl)benzonitrile hydrochloride (3.38 g, 20.0 mmol). The reaction mixture was stirred at room temperature for an additional 1 h and diluted with EtOAc (500 ml). The obtained solution was extracted with water (100 ml), 5% aq. NaHCO3 (100 ml) and water (2×100 ml). The organic layer was dried over MgSO4, evaporated and dried in vacuo to provide compound Q (9.65 g, yield exceeded quantitative) as yellowish oil. LC-MS [M+H] 452.0 (C25H29N3O5+H, calc: 452.4). Compound Q was used without further purification.

Aufarbeitung

  1. extractionThe obtained solution was extracted with water (100 ml), 5% aq. NaHCO3 (100 ml) and water (2×100 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-084c516dfc954c7ea866b61fb543ba10
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040032B2

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