Sodium Hydroxide → tert-butyl N-[(4RS)-4-hydroxymethyl-4,5-dihydro-2-thiazolyl]carbamate
Reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]=[C:11]1[N:15](C(OC(C)(C)C)=O)[CH:14]([CH2:23][O:24]C(OC(C)(C)C)=O)[CH2:13][S:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.O>[OH:24][CH2:23][CH:14]1[CH2:13][S:12][C:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:5])([CH3:4])[CH3:6])=[N:15]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
10 cm3 of aqueous 1N sodium hydroxide are added to a solution of 2 g of tert-butyl 2-[(tert-butoxycarbonyl)imino]-(4RS)-4-[(tert-butoxycarbonyl)oxy]methyl-1,3-thiazolidine-3-carboxylate in 20 cm3 of methanol and the mixture is then stirred at a temperature in the region of 20° C. for 4 hours. The reaction mixture is concentrated under reduced pressure (1 kPa) at a temperature in the region of 50° C. The residue obtained is taken up in 30 cm3 of water, filtered and washed with ethyl acetate and then with water. 0.37 g of tert-butyl N-[(4RS)-4-hydroxymethyl-4,5-dihydro-2-thiazolyl]-carbamate is obtained in the form of a white solid [mass spectrum: DCI m/z=233 MH+ m/z=177 (M-C4H7)+].
Workup
- concentrationThe reaction mixture is concentrated under reduced pressure (1 kPa) at a temperature in the region of 50° C
- customThe residue obtained
- filtrationfiltered
- washwashed with ethyl acetate
Sources & evidence
- ORD record
- ord-24673cadef3c4689a80ab2f65e00eef3
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699895B2
Reaction notes
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