1,2-Dichloroethane → HCID 86659588, compound

HRID 451304Notes

Reaction equation

HRID 451304 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.[NH2:21][C@@H:22]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23]1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>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:21][C@@H:22]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23]1)=[O:20])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 86659588HCID 86659588, 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 (53 mg, 0.192 mmol) in dry dichloromethane (2 mL) was added a solution of tert-butyl (3R)-3-aminopyrrolidine-1-carboxylate (55 mg, 0.288 mmol), triethylamine (0.061 mL, 0.441 mmol), HOBT (44.1 mg, 0.288 mmol), and EDC (55.2 mg, 0.288 mmol) sequentially at room temperature under nitrogen. The reaction was stirred at room temperature for six hours. The reaction mixture was 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.

Workup

  1. concentrationThe reaction mixture was 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-be914ea68ad44b11b151dc1528ff266c
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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