Z-O-tert-butyl-L-serine N-hydroxysuccinimide ester → HCID 178423965, Verbindung

HRID 1910288

Reaktionsgleichung

Reaktionsgleichung von HRID 1910288
CC1C=CC=C2C=1C(=O)N(C1C=CC=CC=1)C(C(NC1N=CN=C3C=1N=CN3)CC)=N2.O=C1CCC(=O)N1OC(=O)C(NC(OCC1C=CC=CC=1)=O)COC(C)(C)C.O=C1CCC(=O)N1OC(=O)C(NC(OCC1C=CC=CC=1)=O)CC.NC1N=C2C(NC=N2)=C(Br)N=1.BrC1N=CN=C2C=1NC=N2.[NH2:105][C:106]1[N:114]=[C:113]2[C:109]([N:110]=[CH:111][NH:112]2)=[C:108]([NH:115][CH:116]([C:123]2[N:132]([C:133]3[CH:138]=[CH:137][CH:136]=[CH:135][CH:134]=3)[C:131](=[O:139])[C:130]3[C:125](=[CH:126][CH:127]=[CH:128][C:129]=3[CH3:140])[N:124]=2)[CH2:117][O:118]C(C)(C)C)[N:107]=1>FC(F)(F)C(O)=O>[NH2:105][C:106]1[N:114]=[C:113]2[C:109]([N:110]=[CH:111][NH:112]2)=[C:108]([NH:115][CH:116]([C:123]2[N:132]([C:133]3[CH:134]=[CH:135][CH:136]=[CH:137][CH:138]=3)[C:131](=[O:139])[C:130]3[C:125](=[CH:126][CH:127]=[CH:128][C:129]=3[CH3:140])[N:124]=2)[CH2:117][OH:118])[N:107]=1

Komponenten

8

Edukt 6

HCID 2729196Z-O-tert-butyl-L-serine N-hydroxysuccinimide esterHCID 5287830Purine, 6-bromo-HCID 61011392-Amino-6-bromopurineHCID 12961228(2,5-Dioxopyrrolidin-1-yl) 2-(phenylmethoxycarbonylamino)butanoateHCID 178423963HCID 178423963, VerbindungHCID 178456854HCID 178456854, Verbindung

Produkt 1

HCID 178423965HCID 178423965, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Compound 68 was prepared using the general procedure described above with respect to compound 14, but 2-benzyloxycarbonylamino-3-tert-butoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester was substituted for 2-benzyloxycarbonylaminobutyric acid 2,5-dioxo-pyrrolidin-1-yl ester in step B, and 2-amino-6-bromopurine was substituted for 6-bromopurine in step D. The obtained 2-[1-(2-amino-9H-purin-6-ylamino)-2-tert-butoxy-ethyl]-5-methyl-3-phenyl-3H-quinazolin-4-one was then dissolved in trifluoroacetic acid and allowed to stir at ambient temperature for 5 hours. Purification by LC provided the product 68 as a white solid. MS (ES): m/z 429 (M+H), 215, 206, 151. Compound 68 is shown below.

Aufarbeitung

  1. customCompound 68 was prepared
  2. customPurification by LC

Quellen und Nachweise

ORD-Eintrag
ord-aacdc7571f1341bc9e9279d2442af4c5
Quelldatensatz
uspto-grants-2013_12
Patentnummer
USRE044638E1

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