Acetic Anhydride → HCID 67383460, compound

HRID 2176934Notes

Reaction equation

HRID 2176934 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]1>N1C=CC=CC=1>[C:1]([NH:8][C@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10464431(1R,3S)-methyl 3-aminocyclopentanecarboxylate

Product 1

HCID 67383460HCID 67383460, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.07 ml, 7.00 mmol) was added to a stirred solution of (1R,3S)-methyl 3-aminocyclopentanecarboxylate (200 mg, 1.39 mmol) in pyridine (5 ml) and stirred for 15 h at ambient temperature. The reaction mixture was concentrated under reduced pressure, water and CHCl3 were added. The organic layer was separated and washed with saturated sodium bicarbonate solution, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 180 mg (69%) of (1R,3S)-methyl 3-acetamidocyclopentanecarboxylate as brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water and CHCl3
  2. additionwere added
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate solution, brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94adc7c8269b4f3a91b48508391f8ce6
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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