(2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acid → HCID 19038612, Verbindung

HRID 263671

Reaktionsgleichung

Reaktionsgleichung von HRID 263671
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][CH:13]([C:43]1[CH:48]=[CH:47][C:46]2[O:49][CH2:50][O:51][C:45]=2[CH:44]=1)[CH:14]([N:16]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[C:17]([CH:19]1[CH:23]([C:24]([O:26]C(C)(C)C)=[O:25])[CH2:22][C:21](=[O:31])[O:20]1)=[O:18])[CH3:15].C(OC(C1CC(=O)OC1C(O)=O)=O)(C)(C)C.C(C([O-])=O)(C([O-])=O)(C([O-])=O)CC>C(O)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][CH:13]([C:43]1[CH:48]=[CH:47][C:46]2[O:49][CH2:50][O:51][C:45]=2[CH:44]=1)[CH:14]([N:16]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[C:17]([CH:19]1[CH:23]([C:24]([OH:26])=[O:25])[CH2:22][C:21](=[O:31])[O:20]1)=[O:18])[CH3:15]

Komponenten

5

Edukt 3

HCID 18705233(2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acidHCID 21864432HCID 21864432, VerbindungHCID 86751027HCID 86751027, Verbindung

Produkt 1

HCID 19038612HCID 19038612, VerbindungAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

47 mg of tert-butyl (2RS,3RS)-2-[N-{(1RS,2RS,4E)-5-(2-benzoxazolyl)-1-methyl-2-(3,4-methylenedioxyphenyl)-4-pentenyl}-N-(2-naphthylmethyl)carbamoyl]-5-oxotetrahydrofuran-3-carboxylate prepared in a manner similar to Example 27 except that (2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acid obtained in Reference Example 4 was used, instead of the 1,2-di-tert-butyl (R*)-1,2,3,-propanetricarboxylate in Example 27, was dissolved in 1 ml of formic acid, and the solution was left to stand at room temperature overnight. The reaction solution was distilled under reduced pressure. Then, toluene was added to the residue, followed by distillation again. The product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)→chloroform/methanol=50/1) to obtain 20 mg (yield: 46%) of the above-identified compound as white solid.

Aufarbeitung

  1. customobtained in Reference Example 4
  2. waitthe solution was left
  3. distillationThe reaction solution was distilled under reduced pressure
  4. additionThen, toluene was added to the residue
  5. distillationfollowed by distillation again
  6. customThe product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)→chloroform/methanol=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-c4894186daa94f939824a44874eca284
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643958

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