Diethyl Ether → (3S,6S,10aS)-6-benzoylamino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid

HRID 1824421Notes

Reaction equation

HRID 1824421 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][CH:5]=[CH: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.CCOCC>O.C1COCC1>[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][CH:5]=[CH:4][CH2:3]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 695843636-Amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid

Product 1

HCID 69584388(3S,6S,10aS)-6-benzoylamino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 6-amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid, 9, (5.6 g, 25 mmol) in 70 mL of H2O/THF solution is then treated with sodium bicarbonate (2.3 g, 27.4 mmol) and benzoyl chloride (3 ml, 25.84 mmol). The reaction is stirred for 18 hours and then ether (100 mL) is added. The organics are washed two times with 1 N HCl, once with water, and dried over MgSO4, filtered, and concentrated in vacuo to a residue which is purified over silica to afford the desired compound which is used without further purification.

Workup

  1. washThe organics are washed two times with 1 N HCl
  2. dry with materialonce with water, and dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a residue which
  5. customis purified over silica

Sources & evidence

ORD record
ord-518853b7d5094d3cbef1a011b9f8854a
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

Loading…