Hydrochloric Acid → HCID 86659582, compound

HRID 451291Notes

Reaction equation

Cl.[CH2:2]([O:9][N:10]([C:29]([O:31]C(Cl)(Cl)Cl)=O)[C@H:11]1[CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[CH2:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C>>[CH2:2]([O:9][N:10]1[C@H:11]2[CH2:15][N:14]([C@H:13]([C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[CH2:12]2)[C:29]1=[O:31])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 8471Triethylamine

HCID 58530056HCID 58530056, compound

Product 1

HCID 86659582HCID 86659582, compound

Procedure

Hydrochloric acid (4.2 M solution in dioxane, 16 mL, 70.4 mmol) was added to 2-allyl 1-tert-butyl (2S,4R)-4-{(benzyloxy)[(trichloromethoxy)carbonyl]amino}-pyrrolidine-1,2-dicarboxylate (80 mg, 1.49 mmol). The resulting mixture was stirred at room temperature overnight then the solvent was removed under vacuum. Dichloromethane (82 mL) was added to the residue followed by triethylamine (0.62 mL, 4.45 mmol). The resulting mixture was stirred at room temperature overnight then the solvent was removed under vacuum. The residue was chromatographed on silica gel (ISCO chromatography system) using a gradient from hexane for 2 minutes to 7:3 hexane:ethyl acetate over 6 minutes, hold for 3 minutes and go to 100% EtOAc over 8 minutes to afford the title compound as a clear oil.

Workup

customthe solvent was removed under vacuum
additionDichloromethane (82 mL) was added to the residue
stirringThe resulting mixture was stirred at room temperature overnight
customthe solvent was removed under vacuum
customThe residue was chromatographed on silica gel (ISCO chromatography system)
customfor 2 minutes
waitethyl acetate over 6 minutes
waithold for 3 minutes
waitgo to 100% EtOAc over 8 minutes

Sources & evidence

ORD record: ord-5151a22c61f049f38bcb9e18e907cceb
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487093B2

Reaction notes

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