Ammonia → HCID 9794760, compound

HRID 915333Notes

Reaction equation

HRID 915333 reaction equation
ClC(OCC(C)C)=O.[O:9]=[C:10]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]([OH:25])=O)[C:11](=[O:17])[C:12]([CH3:16])([CH3:15])[CH2:13][CH3:14].[NH3:26].C(O)C>C(Cl)Cl.O>[O:9]=[C:10]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]([NH2:26])=[O:25])[C:11](=[O:17])[C:12]([CH3:16])([CH3:15])[CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 62365Isobutyl chloroformateHCID 9837656Gpi-1485

Product 1

HCID 9794760HCID 9794760, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Isobutyl chloroformate (20 mmol, 2.7 mL) was added to a solution containing (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidinecarboxylic acid (4.89 g, 20 mmol) (from Example 1) in 50 mL methylene chloride at −10° C. with stirring. After 5 minutes, ammonia was added dropwise (20 mmol, 10 mL of 2 M ethyl alcohol solution). The reaction was warmed up to room temperature after stirring at −10° C. for 30 minutes. The mixture was diluted with water, and extracted into 200 mL methylene chloride. The organic extract was concentrated and further purified by silica gel to give 4.0 g of product as a white solid (81.8% yield). 1H NMR (CDCl3): δ0.91 (t, 3H, J=7.5); 1.28 (s, 6H, each); 1.63–1.84 (m, 2H); 1.95–2.22 (m, 3H); 2.46 (m, 1H); 3.55–3.67 (m, 2H); 4.67 (t, 1H, J=7.8); 5.51–5.53 (br, 1H, NH); 6.80 (br, 1H, NH).

Workup

  1. stirringafter stirring at −10° C. for 30 minutes
  2. extractionextracted into 200 mL methylene chloride
  3. extractionThe organic extract
  4. concentrationwas concentrated
  5. customfurther purified by silica gel

Sources & evidence

ORD record
ord-f224578b5f2f428fa98d2d16d48e619e
Source dataset
uspto-grants-2007_09
Patent number
US07265150B1

Reaction notes

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