Ammonium Chloride → HCID 178456049, compound

HRID 932073Notes

Reaction equation

HRID 932073 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH2:29][CH3:30])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:11](=[O:31])[C@:10]([CH2:33][C:34]#[N:35])([CH3:32])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[N-:36]=[N+:37]=[N-:38].[Na+].[NH4+].[Cl-]>CN(C=O)C>[NH:36]1[C:34]([CH2:33][C@@:10]2([CH3:32])[CH2:9][C@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH2:29][CH3:30])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:11]2=[O:31])=[N:35][N:38]=[N:37]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67999035HCID 67999035, compound

Product 1

HCID 178456049HCID 178456049, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (S)-tert-butyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(cyanomethyl)-3-methyl-2-oxopiperidin-1-yl)butanoate (101 mg, 0.196 mmol; Example 128, Step B) in DMF (0.50 mL) was added sodium azide (127 mg, 1.96 mmol) and NH4Cl (105 mg, 1.96 mmol). The resulting mixture was stirred at 90° C. for 5 days. Then, the reaction was quenched (aq. 10% citric acid), extracted (2×EtOAc), and washed (3×sat. aq. NaCl solution). The combined organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by RP-HPLC (60 to 85% AcCN/H2O, gradient elution) provided the title compound as a white solid.

Workup

  1. customThen, the reaction was quenched (aq. 10% citric acid)
  2. extractionextracted (2×EtOAc)
  3. washwashed (3×sat. aq. NaCl solution)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification
  7. washby RP-HPLC (60 to 85% AcCN/H2O, gradient elution)

Sources & evidence

ORD record
ord-e0427b04c05242f69b78657765c5ab0b
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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