Triethylamine → HCID 86659591, compound

HRID 451312Notes

Reaction equation

HRID 451312 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.[C:37]([NH:44][CH2:45][C:46]1[CH:52]=[CH:51][C:49]([NH2:50])=[CH:48][CH:47]=1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>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:50][C:49]1[CH:51]=[CH:52][C:46]([CH2:45][NH:44][C:37](=[O:38])[O:39][C:40]([CH3:42])([CH3:43])[CH3:41])=[CH:47][CH:48]=1)=[O:20])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 86659591HCID 86659591, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2S,5R)-6-(phenylmethoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (29.9 mg, 0.108 mmol) in dry dichloromethane (3 mL) was added triethylamine (0.038 mL, 0.271 mmol), 2-chloro-1-methylpyridinium iodide (41.0 mg, 0.160 mmol), and 4-(N—BOC-aminomethyl)aniline (30.6 mg, 0.138 mmol) sequentially at room temperature under nitrogen. The reaction was then heated to 60° C. for 2 hours. LC/MS showed no starting material remaining. The reaction mixture was concentrated and purified by HPLC on a Waters Sunfire column to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by HPLC on a Waters Sunfire column

Sources & evidence

ORD record
ord-6b4b8ac294ac4a0bbd7544947c2f6086
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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