Sodium Hydroxide → 2-N-Boc-Amino-Thiazole-5-Carboxylic Acid

HRID 1874006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874006
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 7213140Ethyl 2-((tert-butoxy(hydroxy)methylidene)amino)-1,3-thiazole-5-carboxylate

Produkt 1

HCID 222714422-N-Boc-Amino-Thiazole-5-Carboxylic AcidAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a vigorously stirred suspension of ethyl 2-(tert-butoxycarbonylamino)thiazole-5-carboxylate (4.2 g, 15 mmol) in methanol (11 mL) was added 2 M aqueous solution of NaOH (22 mL, 44.0 mmol). The suspension was stirred at room temperature overnight. The mixture was concentrated in vacuo to remove methanol. The residual aqueous suspension was acidified with 6 N aqueous solution of HCl to pH ˜1-2. The mixture was stirred and occasionally sonicated for 1 hr. The solid was filtered, washed with water, and dried to give 2-(tert-butoxycarbonylamino)thiazole-5-carboxylic acid (3.7 g, 100% yield) as a white solid. MS found: (M+H-Boc)+=145.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove methanol
  3. stirringThe mixture was stirred
  4. customoccasionally sonicated for 1 hr
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-09a7564e41b348dd8398446661c3ba65
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304539B2

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