Ammonium Chloride → HCID 86660718, compound

HRID 931930Notes

Reaction equation

HRID 931930 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C(N(C(C)C)C(C)C)C.N1(C(N2C=CN=C2)=O)C=CN=C1.[Cl:27][C:28]1[CH:29]=[C:30]([C@@H:34]2[C@@H:39]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=3)[N:38]([C@H:47]([CH2:53][CH3:54])[C:48]([O:50][CH2:51][CH3:52])=[O:49])[C:37](=[O:55])[C@@H:36]([CH2:56][C:57](O)=[O:58])[CH2:35]2)[CH:31]=[CH:32][CH:33]=1.[NH4+].[Cl-]>C1COCC1>[Cl:27][C:28]1[CH:29]=[C:30]([C@H:34]2[CH2:35][C@H:36]([CH2:56][C:57]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:58])[C:37](=[O:55])[N:38]([C@@H:47]([CH2:53][CH3:54])[C:48]([O:50][CH2:51][CH3:52])=[O:49])[C@@H:39]2[C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)[CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 68000690HCID 68000690, compound

Product 1

HCID 86660718HCID 86660718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Methanesulfonamide (0.02 g, 0.2 mmol), N-ethyl-N-isopropylpropan-2-amine (0.05 ml, 0.3 mmol), di(1H-imidazol-1-yl)methanone (0.04 g, 0.2 mmol) and 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((R)-1-ethoxy-1-oxobutan-2-yl)-2-oxopiperidin-3-yl)acetic acid (Example 3, 0.030 g, 0.06 mmol) were combined in 2 mL of THF. After being stirred at 25° C. for 12 h, sat. NH4Cl solution was added and the reaction mixture was extracted with EtOAc. The combined organic layers were successively washed with sat. aq. NaHCO3 solution and sat. aq. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by reversed phase HPLC (10 to 90% AcCN/H2O with 0.1% TFA in 45 min) to give the title compound as a white solid.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washThe combined organic layers were successively washed with sat. aq. NaHCO3 solution and sat. aq. NaCl solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by reversed phase HPLC (10 to 90% AcCN/H2O with 0.1% TFA in 45 min)

Sources & evidence

ORD record
ord-cb510a48beee4fb4be90cd168f10ecba
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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