Chloroacetyl chloride → HCID 22115354, compound

HRID 1276365Notes

Reaction equation

HRID 1276365 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[Cl:15][CH2:16][C:17](Cl)=[O:18].C(N(C(C)C)CC)(C)C.C(NC(C)C)(C)C>C(Cl)Cl.C(OCC)(=O)C>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][CH:3]([CH2:2][NH:1][C:17](=[O:18])[CH2:16][Cl:15])[CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chloride2×HCID 7912DiisopropylamineHCID 81531DiisopropylethylamineHCID 2756485tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 22115354HCID 22115354, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3-(RS)-aminomethyl-1-tert-butoxycarbonylpyrrolidine (6.0 g, 30 mmol) in methylene chloride (15 mL) was added dropwise to a cold (0° C.) solution of chloroacetylchloride (2.4 mL, 30 mmol) and diisopropylethylamine (5.5 mL, 32 mmol) in methylene chloride under N2. After 1 h, an additional 0.5 equiv. of chloroacetyl chloride and diisopropylamine were added. After being left at 0° C. overnight, the reaction mixture was diluted with ethyl acetate and washed briefly with water and brine, then dried over sodium sulfate and concentrated to give N-(1-tert-butoxycarbonylpyrrolidin-3-(RS)-ylmethyl)-2-chloroacetamide as a dark brown oil which was used without further purification.

Workup

  1. waitAfter being left at 0° C. overnight
  2. washwashed briefly with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f20c5c0c18d54f5f977dd4158c33b84e
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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