1,2-Dichloroethane → HCID 68812155, compound

HRID 1591670Notes

Reaction equation

HRID 1591670 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=O)[CH2:12][C:10](=[O:11])[CH2:9]1)=[O:7])([CH3:4])[CH3:3].Cl.[F:18][C@H:19]1[CH2:23][CH2:22][NH:21][CH2:20]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[C:2]([O:5][C:6]([N:8]1[CH2:9][C:10](=[O:11])[CH2:12][C@H:13]1[C:14]([N:21]1[CH2:22][CH2:23][C@H:19]([F:18])[CH2:20]1)=[O:16])=[O:7])([CH3:1])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 11593804(2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acidHCID 16217739(s)-3-Fluoropyrrolidine hydrochloride

Product 1

HCID 68812155HCID 68812155, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-tert-Boc-4-oxo-L-proline (2.29 g, 10 mmol), (S)-3-fluoropyrrolidine hydrochloride (1.38 g, 11 mmol) and TEA (2.09 mL, 15 mmol) were mixed in anhydrous methylene chloride (30 mL) under nitrogen. HOBT (2.03 g, 15 mmol) was added and the mixture cooled to 0° C. in an ice bath before addition of EDC (2.10, 11 mmol). The reaction mixture was allowed to warm to RT and stirred overnight. The mixture was washed with saturated sodium bicarbonate and brine and dried over magnesium sulfate. The crude material (3.15 g) was recrystallized from hexane:EtOAc (2:1) to give the title compound as light yellow needles (2.18 g, 73%). MS m/z 301.3 (MH+).

Workup

  1. washThe mixture was washed with saturated sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe crude material (3.15 g) was recrystallized from hexane:EtOAc (2:1)

Sources & evidence

ORD record
ord-e0afe001aff14cf68f491ff0afc051d1
Source dataset
uspto-grants-2007_11
Patent number
US07291618B2

Reaction notes

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