Ammonia → HCID 22220600, compound

HRID 433127Notes

Reaction equation

HRID 433127 reaction equation
N.C([O:5][CH2:6][CH2:7][CH2:8][CH:9]([F:17])[CH2:10][CH2:11][CH2:12][O:13]C(=O)C)(=O)C>CO>[F:17][CH:9]([CH2:10][CH2:11][CH2:12][OH:13])[CH2:8][CH2:7][CH2:6][OH:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 46180112HCID 46180112, compound

Product 1

HCID 22220600HCID 22220600, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (15 ml) saturated with anhydrous NH3 gas was added to acetic acid, 7-acetoxy-4-fluoro-heptyl ester (500 mg, 2.13 mg) contained in round-bottomed flask closed by glass stopper. The mixture was allowed to stir for over 28 hours at room temperature and then concentrated. Purification of the residue by column chromatography on silica gel, using 5% methanol in CH2Cl2, gave the title compound (320 mg, 100%) as pure colorless oil. 1H NMR (CDCl3) δ 1.59-1.83 (m, 8H), 3.67 (t, 4H, J=5.7 Hz), 4.47-4.67 (m, 1H); 13C NMR (CDCl3) δ 28.73, 28.75, 31.78, 32.06, 62.88, 93.56, 95.98; ES-MS m/z 173.2 (M+Na).

Workup

  1. customcontained in round-bottomed flask
  2. customclosed by glass stopper
  3. concentrationconcentrated
  4. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-519690e7cd374761b758395a3975fe4d
Source dataset
uspto-grants-2003_12
Patent number
US06667320B2

Reaction notes

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