1,2-Dichloroethane → HCID 68760397, compound

HRID 451293Notes

Reaction equation

HRID 451293 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][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][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][CH:22]1[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]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 12682914-Amino-1-Boc-piperidineHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 68760397HCID 68760397, 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 (0.141 g, 0.509 mmol) (note: this intermediate is disclosed in U.S. Pat. No. 7,112,592 Example 32b) in dry dichloromethane (3 mL) was added 4-amino-1-BOC-piperidine (0.1532 g, 0.765 mmol), triethylamine (0.16 mL, 1.148 mmol), HOBT (0.1145 g, 0.748 mmol), and EDC (0.1455 g, 0.759 mmol) sequentially at room temperature under nitrogen. The reaction was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue was purified by HPLC (30×100 mm Waters Sunfire column; 5 micron; 35 mL/minute; 210 nM; 15% to 100% CH3CN+0.05% TFA/water+0.05% TFA over 15 minutes; desired product elutes at 50% CH3CN+0.05% TFA/water+0.05% TFA) to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by HPLC (30×100 mm Waters Sunfire column; 5 micron; 35 mL/minute; 210 nM; 15% to 100% CH3CN+0.05% TFA/water+0.05% TFA over 15 minutes; desired product elutes at 50% CH3CN+0.05% TFA/water+0.05% TFA)

Sources & evidence

ORD record
ord-841e5179047c4619bd993de1e370d92e
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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