Riboflavin → (S)-N-(2'-amino-7'-methoxy-5H-spiro[oxazole-4,9'-xanthene]-2-yl)-2,2,2-trifluoroacetamide

HRID 1970310

Reaktionsgleichung

Reaktionsgleichung von HRID 1970310
[N:1]([C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([O:18][CH3:19])=[CH:11][CH:12]=3)[C@:7]3([CH2:23][O:22][C:21]([NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])=[N:20]3)[C:6]=2[CH:5]=1)=[N+]=[N-].CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>C(O)C.C1COCC1.[OH-].[Pd+2].[OH-]>[NH2:1][C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([O:18][CH3:19])=[CH:11][CH:12]=3)[C@:7]3([CH2:23][O:22][C:21]([NH:24][C:25](=[O:30])[C:26]([F:27])([F:29])[F:28])=[N:20]3)[C:6]=2[CH:5]=1

Komponenten

6

Edukt 2

HCID 493570RiboflavinHCID 131730530(s)-n-(2'-Azido-7'-methoxy-5h-spiro[oxazole-4,9'-xanthene]-2-yl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 86640720(S)-N-(2'-amino-7'-methoxy-5H-spiro[oxazole-4,9'-xanthene]-2-yl)-2,2,2-trifluoroacetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (S)—N-(2′-azido-7′-methoxy-5H-spiro[oxazole-4,9′-xanthene]-2-yl)-2,2,2-trifluoroacetamide (0.410 g, 0.978 mmol) in ethanol (12 mL) and THF (8 mL) was stirred with palladium hydroxide, 20 wt % pd (dry basis) on carbon, wet, degussa type e101 ne/w (0.136 g, 0.978 mmol) under hydrogen at atmospheric pressure and RT for 2 hours. The catalyst was removed by filtration over a celite-pad, washed with ethanol (15 mL). The combined filtrates were concentrated to yield the crude product (104584-37-2). The product (S)—N-(2′-amino-7′-methoxy-5H-spiro[oxazole-4,9′-xanthene]-2-yl)-2,2,2-trifluoroacetamide was obtained as an off-white solid. MS (ESI pos. ion) m/z: 394 (M+1).

Aufarbeitung

  1. customThe catalyst was removed by filtration over a celite-pad
  2. washwashed with ethanol (15 mL)
  3. concentrationThe combined filtrates were concentrated
  4. customto yield the crude product (104584-37-2)

Quellen und Nachweise

ORD-Eintrag
ord-94344312674d4ed8bfee31087d4dd038
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426447B2

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