Acetyl chloride → HCID 2825757, compound

HRID 867427Notes

Reaction equation

HRID 867427 reaction equation
[CH3:1][C:2]1([CH3:16])[S:6][C@@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C@H:3]1[C:13]([OH:15])=[O:14].[C:17](Cl)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([N:4]1[C@@H:3]([C:13]([OH:15])=[O:14])[C:2]([CH3:16])([CH3:1])[S:6][C@H:5]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 14548321HCID 14548321, compound

Product 1

HCID 2825757HCID 2825757, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.47 g (2 mmoles) of 5,5-dimethyl-2(S)-phenylthiazolidine-4(S)-carboxylic acid is suspended in 5 ml of pyridine while stirring. The temperature of the suspension is adjusted to 5° C. by cooling with ice-water and 0.17 g of acetyl chloride is dropped in. The mixture is stirred for 1 additional hour, then poured in 60 ml of ice-cold 2N sulphuric acid. After several hours, the precipitated product is filtered out, washed with water and dried. The product is dissolved in ethanol and water is added to precipitate the title compound in a yield of 0.38 g (70.3%), m.p.: 216°-217° C., [α]D20 =-109° (c=0.686, methanol).

Workup

  1. customis adjusted to 5° C.
  2. additionis dropped in
  3. stirringThe mixture is stirred for 1 additional hour
  4. waitAfter several hours
  5. filtrationthe precipitated product is filtered out
  6. washwashed with water
  7. customdried
  8. dissolutionThe product is dissolved in ethanol
  9. additionwater is added
  10. customto precipitate the title compound in a yield of 0.38 g (70.3%), m.p.: 216°-217° C., [α]D20 =-109° (c=0.686, methanol)

Sources & evidence

ORD record
ord-7c8dccdb8c5a48e9a22679beb704e8de
Source dataset
uspto-grants-1988_10
Patent number
US04775675

Reaction notes

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