Triethylamine → (1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 1675409Notes

Reaction equation

HRID 1675409 reaction equation
C(N(CC)CC)C.[I-].[CH2:9]([O:11][C:12]([C@@:14]1([NH:19][C:20](N2C=C[N+](C)=C2)=[O:21])[CH2:16][C@H:15]1[CH:17]=[CH2:18])=[O:13])[CH3:10].[CH2:28]([N:34]([CH3:43])[C:35]([C@@H:37]1[CH2:41][C@@H:40]([OH:42])[CH2:39][NH:38]1)=[O:36])[CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33]>C(Cl)Cl>[CH2:9]([O:11][C:12]([C@@:14]1([NH:19][C:20]([N:38]2[CH2:39][C@H:40]([OH:42])[CH2:41][C@H:37]2[C:35](=[O:36])[N:34]([CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[CH3:43])=[O:21])[CH2:16][C@@H:15]1[CH:17]=[CH2:18])=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57816715(2S,4R)-N-(hex-5-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamideHCID 866332061-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl-carbamoyl)-3-methyl-1H-imidazol-3-ium iodide

Product 1

HCID 66650543(1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.3 mL, 3 eq.) was added at room temperature under nitrogen to a mixture of compound 34 (0.7 g, 1 eq.) and compound 49 (1.2 g, 1 eq.) in DCM (15 mL). The reaction mixture was stirred overnight at room temperature and then quenched with 1M aqueous hydrochloric acid. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to yield compound 50 as a white solid in 70% yield.

Workup

  1. customquenched with 1M aqueous hydrochloric acid
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1d98916a4f124a0db5ccd2917722d979
Source dataset
uspto-grants-2011_08
Patent number
US08003659B2

Reaction notes

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