Water → Benzyl 4'-benzyloxycarbonylamino-2'-methoxymethyloxycarbonyl-4-hydroxymethyl-2-biphenylcarboxylate

HRID 277981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277981
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:43]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:44])=[CH:20][C:21]([CH2:24][O:25][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:22][CH:23]=2)=[C:14]([C:53]([O:55][CH2:56][O:57][CH3:58])=[O:54])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(NC1C=C(C(O)=O)C(O)=CC=1)=O)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:43]([O:45][CH2:46][C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[O:44])=[CH:20][C:21]([CH2:24][OH:25])=[CH:22][CH:23]=2)=[C:14]([C:53]([O:55][CH2:56][O:57][CH3:58])=[O:54])[CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 103567045-{[(Benzyloxy)carbonyl]amino}-2-hydroxybenzoic acidHCID 70163839Benzyl 4'-benzyloxycarbonylamino-2'-methoxymethyloxycarbonyl-4-t-butyidiphenylsilyloxymethyl-2-biphenyl carboxylate

Produkt 1

HCID 22626197Benzyl 4'-benzyloxycarbonylamino-2'-methoxymethyloxycarbonyl-4-hydroxymethyl-2-biphenylcarboxylateAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of benzyl 4′-benzyloxycarbonylamino-2′-methoxymethyloxycarbonyl-4-t-butyidiphenylsilyloxymethyl-2-biphenyl carboxylate (777 mg) which was prepared by the same procedure as a series of reaction of Reference Example 6→Reference Example 1 (without an esterfication of benzyl)→Reference Example 4→Reference Example 5→Reference Example 7, using 5-benzyloxycarbonylaminosalicylic acid; in anhydrous tetrahydrofuran (10 ml), a solution of 1.0 M tetrabutylammonium fluoride in anhydrous tetrahydrofuran (1.0 ml) was added. The mixture was stirred for 2 hours at room temperature. Water (100 ml) was added to the reaction mixture, the solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:3) to give the title compound (370 mg) having the following physical data.

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:3)

Quellen und Nachweise

ORD-Eintrag
ord-9f486ddd75974d5e9c7c5191c916293a
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358960B1

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