ChemicalBook CAS DataBase List (5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone

(5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone synthesis

5synthesis methods

Product Name:(5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone
CAS Number:1095565-81-3
Molecular formula:C14H22N2OS
Molecular Weight:266

4(5H)-Thiazolone, 2-[(1S,2S,4R)-bicyclo[2.2.1]hept-2-ylaMino]-5-Methyl-5-(1-Methylethyl)-, (5S)- (Methanesulfonate)

1095565-87-9
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(5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone

1095565-81-3
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Yield:1095565-81-3 95.1%

Reaction Conditions:

with sodium hydroxide;water in dichloromethane; for 1 h;Purification / work up;

Steps:

7.4

Step 4 (Free basing); [0154] To a 40 g suspension of MSA salt (20) in DCM (1OX, 40OmL) in a 1000 mL, 3 neck round bottom flask, equipped with a mechanical stirrer and a nitrogen inlet, was added 5X of IN NaOH (200 mL). The mixture was stirred for 1 hour and transferred to a separatory funnel. The layers were allowed to settle for 15 minutes and then split. The organic layer was then washed with 5 volumes of DI water until the pH of the aqueous layer was neutral. The organic layer (DCM) is filtered through a medium fritted glass filter prior to proceeding with the solvent exchange. [0155] An atmospheric distillation was performed in order to reduce the volume of DCM to a level of 3.75X (150 mL). At this point, IPA (3.75X; 150 mL) was introduced into the flask and the atmospheric distillation was resumed until the volume of the batch reached once again 3.75X (150 mL). An additional 3.75X (150 mL) IPA was introduced to the flask and distillation was continued until the final volume of the batch was 3.75X (150 mL). The batch temperature during this stage was equivalent to the boiling point of IPA (-82 °C). To the hot solution (75+/-5 °C) of product in IPA was added water (3 X; 120 mL) at such a rate that the temperature is maintained above 70 °C. The mixture was cooled to 5°C over a >1 hour period and held for 75 minutes. The solids were filtered, and washed with a minimum amount (~2X) of cold (5 ⁰C) IP A/water mixture (40/60). The solid was dried in a vacuum oven at 55 °C for 17 hours. Isolated 27.97 g of product (19) (95.1% uncorrected yield; 99.76 % de).

References:

WO2009/2445,2008,A1 Location in patent:Page/Page column 47-48