Benzoyl chloride → HCID 58632018, compound

HRID 1824428Notes

Reaction equation

HRID 1824428 reaction equation
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:11]([C:14]([OH:16])=[O:15])[CH2:12][CH2:13][CH:7]2[CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O.C(Cl)Cl.CCOCC>[C:22]([NH:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][CH2:13][C@@H:7]2[CH2:6][CH2:5][CH2:4][CH2:3]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 22149056HCID 22149056, compound

Product 1

HCID 58632018HCID 58632018, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21908982Water methylene chlorideSolvent

Procedure

A solution of 6-amino-5-oxo-decahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid, 19, (181 mg, 0.8 mmol) in H2O/CH2Cl2 (7 mL) is treated with sodium bicarbonate (0.50 g, 6 mmol) and benzoyl chloride (140 mg, 1.0 mmol). The reaction is stirred for 18 hours then diluted with ether (100 mL). The organic layer is washed twice with 1 N HCl, once with water, and dried over MgSO4, filtered, and concentrated under in vacuo to afford a residue which is purified over silica to afford the desired compound.

Workup

  1. washThe organic layer is washed twice with 1 N HCl, once with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under in vacuo
  5. customto afford a residue which
  6. customis purified over silica

Sources & evidence

ORD record
ord-1e8527fd89f04f158ac5a6de2c877ded
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

Loading…