N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[t-butyloxycarbonylaminosulfonyl]-amino-acetic acid ethyl ester → N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester

HRID 1592039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592039
[CH2:1]([O:3][C:4](=[O:46])[CH2:5][N:6]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]2[NH:31][C:30](=[O:32])[C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[NH:27][C:26]2=[O:37])=[CH:20][C:19]=1[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[S:7]([NH:10]C(OC(C)(C)C)=O)(=[O:9])=[O:8])[CH3:2]>C(Cl)Cl.FC(C(O)=O)(F)F.C([SiH](CC)CC)C>[CH2:1]([O:3][C:4](=[O:46])[CH2:5][N:6]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]2[NH:31][C:30](=[O:32])[C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[NH:27][C:26]2=[O:37])=[CH:20][C:19]=1[O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[S:7]([NH2:10])(=[O:8])=[O:9])[CH3:2]

Komponenten

3

Edukt 1

HCID 67139078N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[t-butyloxycarbonylaminosulfonyl]-amino-acetic acid ethyl ester

Produkt 1

HCID 67138957N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 131726667triethylsilane TFA DCMLösungsmittel

Versuchsvorschrift

The title M compound, N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[t-butyloxycarbonylaminosulfonyl]-amino-acetic acid ethyl ester (124 mg, 0.19 mmol) is dissolved in CH2Cl2-TFA-triethylsilane (2.5:7:0.5, 1.5 mL) and the solution is stirred at RT for 1 h and evaporated. The residue is dissolved in EtOAc and the solution is washed twice with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and evaporated to give N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester as a foam: [M+1]+=553.

Aufarbeitung

  1. customevaporated
  2. dissolutionThe residue is dissolved in EtOAc
  3. washthe solution is washed twice with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0226e1e54e924b35a89176880e0c9376
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291635B2

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