Phenylacetyl chloride → HCID 86631064, compound

HRID 38281Notes

Reaction equation

HRID 38281 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[C:4]([CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH:20]([CH3:24])[CH:19]2[CH3:25])[CH:3]=1.C(=O)(O)[O-].[Na+].[C:31]1([CH2:37][C:38](Cl)=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[C:4]([CH2:17][N:18]2[CH2:23][CH2:22][N:21]([C:38](=[O:39])[CH2:37][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:20]([CH3:24])[C@@H:19]2[CH3:25])[CH:3]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 86631065HCID 86631065, compound

Product 1

HCID 86631064HCID 86631064, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred solution/suspension of the product from example 71 part a) (0.189 g) and solid sodium bicarbonate (0.215 g) in DCM (2 ml) and water (2 ml) was added phenylacetyl chloride (0.14 ml) dropwise. The mixture was stirred for 2 h. The organic layer and 1 further DCM extract were combined, dried (Na2SO4) and purified by passage through SCX resin eluting with MeCN, MeOH followed by 7M NH3 in MeOH. The basic fractions were concentrated in vacuo to give the sub-titled product as a white foam (0.205 g).

Workup

  1. extractionThe organic layer and 1 further DCM extract
  2. dry with materialdried (Na2SO4)
  3. custompurified by passage through SCX resin
  4. washeluting with MeCN, MeOH
  5. concentrationThe basic fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-c55865f6b6e7439f859740be1e2ada27
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

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