Acetyl chloride → trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

HRID 21967

Reaction equation

HRID 21967 reaction equation
[SH:1][CH2:2][C@H:3]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([C:13]([OH:15])=[O:14])[NH:5][C:4]1=[O:16].[C:17](Cl)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([S:1][CH2:2][C@H:3]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([C:13]([OH:15])=[O:14])[NH:5][C:4]1=[O:16])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86747203Trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxylic acid

Product 1

HCID 86747202trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxylic acid (0.75 g, 3.06 mmol) is dissolved in pyridine (20 mL). Acetyl chloride (0.26 g, 3.37 mmol) is added, and the reaction is stirred at room temperature overnight. The reaction is quenched by cooling to 0° C., adding concentrated hydrochloric acid (20 mL), diluting with water, and extracting several times with ethyl acetate. The combined organic layers are dried (MgSO4), and the solvent is evaporated to give trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid, MS: M+1=288.

Workup

  1. customThe reaction is quenched
  2. temperatureby cooling to 0° C.
  3. additionadding concentrated hydrochloric acid (20 mL)
  4. additiondiluting with water
  5. extractionextracting several times with ethyl acetate
  6. dry with materialThe combined organic layers are dried (MgSO4)
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-59dc5b80135948aba5d46d8e397c7604
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Linked notes

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