Potassium tert-butoxide → HCID 54495068, compound

HRID 1871719Notes

Reaction equation

HRID 1871719 reaction equation
[CH3:1][C:2]([O-:5])([CH3:4])[CH3:3].[K+].OC1[CH:9]=[C:10]([CH:14]=C(O)C=1)[C:11]([O-])=O.[C:18]([C@H:21]1[CH2:25][CH2:24][CH2:23][N:22]1[C:26](=[O:51])[CH2:27][O:28][C:29]1[CH:30]=[C:31]([CH:44]=[C:45]([C:47]([O:49][CH3:50])=[O:48])[CH:46]=1)[O:32][CH2:33][C:34]([N:36]1[CH2:40][CH2:39][CH2:38][C@@H:37]1[C:41]([OH:43])=O)=[O:35])([OH:20])=[O:19]>CN(C)C=O>[C:2]([O:5][C:41]([C@H:37]1[CH2:38][CH2:39][CH2:40][N:36]1[C:34](=[O:35])[CH2:33][O:32][C:31]1[CH:44]=[C:45]([C:47]([O:49][CH3:50])=[O:48])[CH:46]=[C:29]([O:28][CH2:27][C:26]([N:22]2[CH2:23][CH2:24][CH2:25][C@@H:21]2[C:18]([O:20][C:10]([CH3:14])([CH3:11])[CH3:9])=[O:19])=[O:51])[CH:30]=1)=[O:43])([CH3:4])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 53991922HCID 53991922, compoundHCID 178524612HCID 178524612, compound

Product 1

HCID 54495068HCID 54495068, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 595 mg (5.3 mmol) potassium tert-butylate in 4 ml dimethylformamide at room temperature was added dropwise a solution of 420 mg (2.5 mmol) 3,5-dihydroxybenzoate in 4 ml dimethylformamide. Stirring was continued for 2-3 min and a solution of 1.46 mg (5.0 mmol) (R)- (1)-bromoacetyl-pyrrolidine-2-carboxylic acid tert-butyl ester in 5 ml dimethylformamide was added within 1-2 min. The reaction mixture was stirred for additional 2 h at room temperature. The solvent was removed in vacuo and the residue purified by flash-chromatography to yield 1.01 g (68%) of the title compound as a colorless oil. MS m/e (%): 608 (M+NH4+, 92), 591 (M+H+, 48), 535 (41), 479 (100).

Workup

  1. stirringThe reaction mixture was stirred for additional 2 h at room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by flash-chromatography

Sources & evidence

ORD record
ord-d9b78c82e5394f2d87518e87e5715404
Source dataset
uspto-grants-2000_08
Patent number
US06103910

Reaction notes

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