Ammonia → HCID 69025297, compound

HRID 349365Notes

Reaction equation

HRID 349365 reaction equation
C([N:3](CC)CC)C.ClC(OCC)=O.[OH:14][CH:15]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)/[CH:16]=[CH:17]/[C@H:18]1[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[N:19]1[CH2:25][C:26]#[C:27][CH2:28][O:29][CH2:30][C:31](O)=[O:32].N.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:14][CH:15]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)/[CH:16]=[CH:17]/[C@H:18]1[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[N:19]1[CH2:25][C:26]#[C:27][CH2:28][O:29][CH2:30][C:31]([NH2:3])=[O:32]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 69022915HCID 69022915, compound

Product 1

HCID 69025297HCID 69025297, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (9.4 μL, 0.067 mmol) and ethyl chloroformate (3.1 μL, 0.032 mmol) were added sequentially to a solution of {4-[(R)-2-((E)-3-hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-but-2-ynyloxy}-acetic acid (11.8 mg, 0.032 mmol) in CH2Cl2 (0.2 mL) at 0° C. After 1 h at 0° C., ammonia (0.5 M in 1,4-dioxane, 0.32 mL, 0.16 mmol) was added and the reaction mixture was allowed to warm to rt. After 17 h at rt, the reaction mixture was treated with saturated aqueous NaHCO3 (10 mL) and extracted with CH2Cl2 (3×10 mL). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford 11 mg (93%) of the title compound.

Workup

  1. waitAfter 17 h at rt
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69a17430e5f546118c158ea3cd208ace
Source dataset
uspto-grants-2007_02
Patent number
US07179820B2

Reaction notes

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