tert-butyl (2-formylthiazol-5-yl)carbamate synthesis

4synthesis methods

Product Name:tert-butyl (2-formylthiazol-5-yl)carbamate
CAS Number:1094070-79-7
Molecular formula:C9H12N2O3S
Molecular Weight:228.27

tert-butyl (2-vinylthiazol-5-yl)carbamate

1094070-78-6
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tert-butyl (2-formylthiazol-5-yl)carbamate

1094070-79-7
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Yield:1094070-79-7 92%

Reaction Conditions:

with 2,6-dimethylpyridine;sodium periodate;osmium(VIII) oxide in 1,4-dioxane;water;isopropyl alcohol; for 4 h;

Steps:

40.C

Part C: To a stirred solution of (2-Vinyl-thiazol-5-yl)-carbamic acid tert-butyl ester (0.76 g, 2.857 mmol) in 1 ,4-dioxane : water (30 : 9 mL), were added sodium periodate (2.5 g, 11.43 mmol) osmium tetroxide (2.5% solution in 2-propanol) (0.5 mL) and 2,6- lutidine (0.663 mL, 5.714 mmol) and reaction mixture was stirred for 4 hrs, LCMS showed the almost disappearance of the starting material. Reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate, organic layer was washed with water, brine, dried over sodium sulfate and concentrated under high vacuum to yield aldehyde 710 mg (92%). Crude product was used as such in the next reaction. 1H NMR (400 MHz, DMSO-d6 δ 11.45 (s, 1 H), 9.76 (s, 1 H), 7.58 (s, 1 H), 1.40 (s, 9H). Mass calculated for formula C9H12N2O3S 228.06; observed MH+ (LCMS) 229.1 (m/z).

References:

WO2008/156614,2008,A2 Location in patent:Page/Page column 125; 126

(2-Hydroxymethyl-thiazol-5-yl)-carbamic acid tert-butyl ester

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References

1246549-82-5 Synthesis

5-tert-Butoxycarbonylamino-thiazole-2-carboxylic acid ethyl ester

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1094070-79-7
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References

1094070-77-5
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$36.00/100mg

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References