Acetic Anhydride → (S)-4-(acetylamino)-5-fluoropentanoic acid, methyl ester

HRID 370620Notes

Reaction equation

HRID 370620 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:18])[CH2:12][CH2:13][C@H:14]([NH2:17])[CH2:15][F:16].[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(O)(=O)C>[C:19]([NH:17][C@H:14]([CH2:15][F:16])[CH2:13][CH2:12][C:11]([O:10][CH3:9])=[O:18])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 131714255(S)-4-amino-5-fluoropentanoic acid methyl ester, hydrochloride

Product 1

HCID 13477555(S)-4-(acetylamino)-5-fluoropentanoic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

0.26 ml of triethylamine and 2 ml of glacial acetic acid were mixed with 0.34 g of 4. The mixture was cooled to 0° C. and 0.21 ml of acetic anhydride was added drop-by-drop to the stirred mixture. The mixture was allowed to warm to room temperature and stirred for 30 minutes. The solvents were evaporated under reduced pressure, the residue was triturated with a mixture of ethyl acetate and ether and filtered. The filtrate was eluted through a florisil pad, using ethyl acetate as eluent. The solvent was evaporated under reduced pressure to give 6, as a brown solid.

Workup

  1. temperatureto warm to room temperature
  2. customThe solvents were evaporated under reduced pressure
  3. customthe residue was triturated with a mixture of ethyl acetate and ether
  4. filtrationfiltered
  5. washThe filtrate was eluted through a florisil pad
  6. customThe solvent was evaporated under reduced pressure
  7. customto give 6

Sources & evidence

ORD record
ord-a5d5670ede44466ea5141c263b072ce7
Source dataset
uspto-grants-1985_07
Patent number
US04528028

Reaction notes

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