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4-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)morpholine-2-carboxylic acid (500 mg, 1 mmol) (see following steps B and C for preparation) was dissolved in DMF (10 mL). Ethylamine hydrochloride (122 mg, 1.5 mmol) and N,N-diisopropylethylamine (1 mL, 5 mmol) were added and the reaction mixture was cooled down to 0° C. HATU (456 mg, 1.2 mmol) was added portionwise and the reaction was stirred overnight at room temperature. The reaction was concentrated, extracted with EtOAc and washed with sodium bicarbonate, water then brine and dried over anhydrous sodium sulfate. The crude product was purified by LCMS using high pH column 40-70% acetonitrile gradient to give 200 mg (40%) as white solid racemic mixture of the title compound. The two enantiomers were separated on a chiral OD 5 microns column using 20% ethanol/hexane. Example 112 (isomer-1): 1H NMR (400 MHz, METHANOL-D4) δ 1.04 (t, J=7.23 Hz, 3 H), 1.46-1.56 (m, 2 H), 1.57 (s, 9 H), 1.61-1.70 (m, 3 H), 1.70-1.81 (m, 1 H), 1.98-2.08 (m, 2 H), 2.12-2.23 (m, 1 H), 2.39 (m, 1 H), 2.74 (q, J=7.23 Hz, 2 H), 3.17 (dd, J=7.23, 3.91 Hz, 2 H), 3.68 (m, 1 H), 3.87-3.94 (m, 1 H), 4.01 (dd, J=10.45, 2.83 Hz, 2 H), 4.40 (d, J=7.62 Hz, 2 H), 7.64 (dd, J=8.59, 1.56 Hz, 1 H), 7.77 (d, J=8.59 Hz, 1 H), 8.03 (d, J=1.76 Hz, 1 H); MS (APPI) (M+H)+=527.3; Anal. Calc. for C21H29F2N3O3S+4.9C2HO2F3+5.0H2O+2.7 CH3CN: C, 39.47; H, 4.14; N, 6.31. Found: C, 39.48; H, 4.14; N, 6.30.

1. concentrationThe reaction was concentrated
2. extractionextracted with EtOAc
3. washwashed with sodium bicarbonate, water
4. dry with materialbrine and dried over anhydrous sodium sulfate
5. customThe crude product was purified by LCMS
6. customto give 200 mg (40%)