(S)-2-(3-(1-(tert-butylsulfonylMethyl)cyclohexyl)ureido)-3,3-diMethylbutanoic acid synthesis
- Product Name:(S)-2-(3-(1-(tert-butylsulfonylMethyl)cyclohexyl)ureido)-3,3-diMethylbutanoic acid
- CAS Number:1208245-85-5
- Molecular formula:C18H34N2O5S
- Molecular Weight:390.54
![Carbamic acid, N-[1-[[(1,1-dimethylethyl)sulfonyl]methyl]cyclohexyl]-, phenyl ester](/CAS/20210111/GIF/1263416-49-4.gif)
Yield:1208245-85-5 94%
Reaction Conditions:
Stage #1: L-tert-Leucine;C18H27NO4S in isopropyl alcohol at 70; for 1.5 h;Industry scale;
Stage #2: with hydrogenchloride in water;isopropyl alcohol at 22; pH=<= 1.5;Industry scale;
Steps:
Preparation of Compound Vl (via VIO) Compound VIO (34.6 kg, 1 eq.) and L-te/f-Ieucine ()12.8 kg, 1 eq.) were added to stirred isopropanol and the mixture was heated to 70 +/- 3 0C. Over about 30 min, tetramethyl guanidine (12.5 kg, 1.1 eq.) was added while maintaining the temperature at 70 +/- 3 0C. After 1 h, the mixture was cooled to 60 +/- 3 0C. Water (237 L) was added and the mixture was cooled to 22 +/- 3 0C. Maintaining the temperature, the pH was adjusted to < 1.5 with HCI (13 L). Once crystallization began, the mixture was cooled to 2 +/- 3 0C and maintained at that temperature for 1 h. The solids were isolated by centrifugation, washed with water (2 X 35 L) and dried at 50 0C. A 94% yield of compound Vl was achieved.
References:
WO2011/14494,2011,A1 Location in patent:Page/Page column 49
![Cyclohexane, 1-[[(1,1-dimethylethyl)sulfonyl]methyl]-1-isocyanato-](/CAS/20210305/GIF/848776-92-1.gif)
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