1,2-Dichloroethane → HCID 86699449, compound

HRID 451317Notes

Reaction equation

HRID 451317 reaction equation
[C:1]1([CH2:7][O:8][N:9]2[C:15](=[O:16])[N:14]3[CH2:17][C@H:10]2[CH2:11][CH2:12][C@H:13]3[C:18]([OH:20])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.C(Cl)CCl.[NH2:34][C@H:35]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36]1>ClCCl>[CH2:7]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([NH:34][C@H:35]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36]1)=[O:20])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 218852-DimethylaminopyridineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 86699449HCID 86699449, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,5R)-6-(phenylmethoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (1 g, 3.62 mmol) in dry dichloromethane (30 mL) was added dimethylaminopyridine (884 mgL, 7.24 mmol), EDC (1.388 g, 7.24 mmol), and tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate (742 mg, 3.98 mmol) sequentially at room temperature under nitrogen. The reaction mixture was stirred at room temperature over the weekend. The reaction mixture was then concentrated under vacuum and the residue was purified by HPLC on a 30×100 mm Waters Sunfire column eluted with 15% to 100% CH3CN+0.05% TFA/water+0.05% TFA over 15 minutes to afford the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. customthe residue was purified by HPLC on a 30×100 mm Waters Sunfire column
  3. washeluted with 15% to 100% CH3CN+0.05% TFA/water+0.05% TFA over 15 minutes

Sources & evidence

ORD record
ord-dc90514f15944693baf4c010e81910da
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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