Triethylamine → (2S,5R)-6-(Benzyloxy)-N-[2-(dimethylamino)pyridin-4-yl]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

HRID 451310Notes

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.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C.[CH3:37][N:38]([CH3:46])[C:39]1[CH:44]=[C:43]([NH2:45])[CH:42]=[CH:41][N:40]=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:45][C:43]1[CH:42]=[CH:41][N:40]=[C:39]([N:38]([CH3:46])[CH3:37])[CH:44]=1)=[O:20])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (2S,5R)-6-(phenylmethoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (37.3 mg, 0.135 mmol) in dry dichloromethane (2.5 mL) was added triethylamine (0.047 mL, 0.338 mmol), 2-chloro-1-methylpyridinium iodide (38.3 mg, 0.15 mmol), and 2-dimethylamino-4-aminopyridine (21.7 mg, 0.158 mmol) sequentially at room temperature under nitrogen. The reaction was then heated to 50° C. for 1.5 hours. LC/MS showed reaction complete. The reaction mixture was concentrated and purified by HPLC on a 30×100 mm Waters Sunfire column to afford the title compound as an off-white solid after lyophilization.

Workup

customreaction complete
concentrationThe reaction mixture was concentrated
custompurified by HPLC on a 30×100 mm Waters Sunfire column

Sources & evidence

ORD record: ord-ea2f442a8d814c7a84f3e536085aedaf
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487093B2

Reaction notes

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