Sodium Hydroxide → 4-(((1R,3S)-3-((tert-butoxycarbonyl)amino)-2,2,3-trimethylcyclopentyl)amino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylic acid

HRID 1408984

Reaktionsgleichung

Reaktionsgleichung von HRID 1408984
[C:1]([O:5][C:6]([NH:8][C@@:9]1([CH3:34])[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]2[C:16]3[N:17]([CH:24]=[C:25]([C:27]([O:29]CC)=[O:28])[CH:26]=3)[N:18]=[CH:19][C:20]=2[C:21](=[O:23])[NH2:22])[C:10]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][C@@:9]1([CH3:34])[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]2[C:16]3[N:17]([CH:24]=[C:25]([C:27]([OH:29])=[O:28])[CH:26]=3)[N:18]=[CH:19][C:20]=2[C:21](=[O:23])[NH2:22])[C:10]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 14798Sodium Hydroxide3×HCID 86707717ethyl 4-((1R,3S)-3-(tert-butoxycarbonylamino)-2,2,3-trimethylcyclopentylamino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylate

Produkt 1

HCID 867077164-(((1R,3S)-3-((tert-butoxycarbonyl)amino)-2,2,3-trimethylcyclopentyl)amino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylic acidAusbeute 112,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of ethyl 4-((1R,3S)-3-(tert-butoxycarbonylamino)-2,2,3-trimethylcyclopentylamino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylate (10.62 g, 22.42 mmol) and 1 N NaOH (120 mL) in THF (100 mL) and MeOH (100 mL) was heated to 60° C. for 16 hrs. and then the reaction mixture was added 120 ml of 1 N NaOH solution and heated to 70° C. for 8 hrs. The reaction mixture was added 120 ml of 1 N NaOH solution and heated to 70° C. for 8 hrs which was concentrated to remove THF and MeOH. The aqueous layer was acidified with conc. HCl solution until pH about 4 at 0-5° C. The solid was collected to give 4-(((1R,3S)-3-((tert-butoxycarbonyl)amino)-2,2,3-trimethylcyclopentyl)amino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylic acid (11.2 g, 76% yield). HPLC retention time=3.020 min., LC/MS (M+H)+=446.3.

Aufarbeitung

  1. temperatureheated to 70° C. for 8 hrs which
  2. concentrationwas concentrated
  3. customto remove THF and MeOH
  4. customwas acidified with conc. HCl solution until pH about 4 at 0-5° C
  5. customThe solid was collected

Quellen und Nachweise

ORD-Eintrag
ord-84bca8cbd5ac4b1d814801fa8a27a16e
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921368B2

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