4-(Benzyloxy)benzoic acid → HCID 11566766, compound

HRID 642184Notes

Reaction equation

HRID 642184 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N=C=N.[NH:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>CN(C=O)C.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:21]2[CH2:25][CH2:24][CH2:23][C@H:22]2[CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 738804-(Benzyloxy)benzoic acidHCID 160435CarbodiimideHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine

Product 1

HCID 11566766HCID 11566766, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-benzyloxybenzoic acid (116 mg, 0.51 mmol) and PS-carbodiimide (500 mg, 0.66 mmol, 1.32 mmol/g) in 5% DMF in CH2Cl2 (5 mL) is added (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (80 mg, 0.51 mmol). The mixture is stirred at room temperature for 3 days. The reaction mixture is filtered, and the resin is washed with CH2Cl2. The filtrate is concentrated and applied to silica-gel column chromatography (in CH2Cl2 followed by 5% 2M NH3 in MeOH/CH2Cl2) to give the product. 62.7 mg (34%): Observed mass: 365 (M+1).

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe resin is washed with CH2Cl2
  3. concentrationThe filtrate is concentrated
  4. customto give the product

Sources & evidence

ORD record
ord-c9dddc1033d148b2bc50ad1db04c7177
Source dataset
uspto-grants-2010_04
Patent number
US07696234B2

Reaction notes

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