Triethylamine → t-butyl N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]phenyl]-N-methylcarbamate

HRID 412376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412376
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:11]([CH3:24])[CH:10]=2)=[CH:4][C:3]=1[N:25]([CH3:33])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].[O:34]=[C:35]1[NH:39][C:38](=[O:40])[CH:37]([CH2:41][C:42]2[CH:52]=[CH:51][C:45]([O:46][CH2:47][C:48](O)=[O:49])=[CH:44][CH:43]=2)[S:36]1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>O1CCCC1>[C:20]([O:19][C:17]([NH:16][C:12]1[C:13]([CH3:15])=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:48](=[O:49])[CH2:47][O:46][C:45]3[CH:44]=[CH:43][C:42]([CH2:41][CH:37]4[S:36][C:35](=[O:34])[NH:39][C:38]4=[O:40])=[CH:52][CH:51]=3)=[C:3]([N:25]([CH3:33])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:4]=2)=[CH:10][C:11]=1[CH3:24])=[O:18])([CH3:22])([CH3:23])[CH3:21]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidHCID 18184919t-Butyl N-[2-amino-5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)phenyl]-N-methylcarbamate

Produkt 1

HCID 18537724t-butyl N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]phenyl]-N-methylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of t-butyl N-[2-amino-5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)phenyl]-N-methylcarbamate (1.56 g), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (1.05 g), diethyl cyanophosphonate (0.61 g), triethylamine (0.38 g) and anhydrous tetrahydrofuran (30 ml) was stirred at room temperature for 19 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=1:1 as the eluant to afford the desired compound (1.89 g, Rf=0.19: thin layer chromatography on a silica gel plate using ethyl acetate:n-hexane=2:3 as the eluant).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-a1460f65054f4c5c9e35559b42d9ad54
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562849B1

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