1-Hydroxybenzotriazole → HCID 86699614, compound

HRID 2400667Notes

Reaction equation

HRID 2400667 reaction equation
[CH2:1]([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]([OH:20])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][C:26](=[O:36])[NH:27][CH2:28][C@H:29]1[CH2:33][CH2:32][C@H:31]([O:34][NH2:35])[CH2:30]1)([CH3:24])([CH3:23])[CH3:22].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[C:21]([O:25][C:26](=[O:36])[NH:27][CH2:28][C@H:29]1[CH2:33][CH2:32][C@H:31]([O:34][NH:35][C:18]([C@@H:13]2[CH2:12][CH2:11][C@@H:10]3[CH2:17][N:14]2[C:15](=[O:16])[N:9]3[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:20])[CH2:30]1)([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acidHCID 86699613HCID 86699613, compound

Product 1

HCID 86699614HCID 86699614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 1 (0.25 g, 0.90 mmol, US2005/20572 A1, 2005) in DCM (20 was added tert-butyl[trans-3-(aminooxy)cyclopentyl]methylcarbamate 116 (0.32 g, 1.39 mmol), 1-hydroxybenzotriazole (0.18 g, 1.33 mmol), and 1-ethyl-(3-dimethylamino propyl) carbodiimide hydrochloride (0.26 g, 1.36 mmol) sequentially at room temperature. The mixture was stirred at room temperature for 6 hours, then concentrated in vacuo to provide a residue which was subjected to chromatography to give 117 (0.45 g, contains some byproduct) as a white foam.

Workup

  1. concentrationconcentrated in vacuo
  2. customto provide a residue which

Sources & evidence

ORD record
ord-ebcf602f6f3d4ddb8375ae8b16969577
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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