Lithium hydroxide, monohydrate → 4-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 2361294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361294
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:42])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:37]([O:39]CC)=[O:38])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:42])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([N:31]5[CH2:32][CH2:33][O:34][CH2:35][CH2:36]5)=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:37]([OH:39])=[O:38])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 67994966Ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylate

Produkt 1

HCID 679946444-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylate (0.3539 g, 0.627 mmol) in THF (17.4 mL) and MeOH (5.8 mL) was added a solution of lithium hydroxide hydrate (0.105 g, 2.507 mmol) in water (3 mL). After 1 hr, the reaction was concentrated in vacuo. Water (12 mL) was added, and the solution was acidified with aqueous 1N HCl to pH 5-6 by litmus paper. The precipitate was filtered, washed with water, dried over Drierite to give the desired product (0.286 g, 0.533 mmol, 85% yield) as an orange solid.

Aufarbeitung

  1. concentrationthe reaction was concentrated in vacuo
  2. additionWater (12 mL) was added
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. dry with materialdried over Drierite

Quellen und Nachweise

ORD-Eintrag
ord-fb216d51976e4d0f9ee63fac92535d40
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685969B2

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