4-(4-Aminophenyl)butanoic acid → HCID 54758960, compound

HRID 926818Notes

Reaction equation

HRID 926818 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.Cl[C:15]([O:17][CH2:18][CH:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16]>C(=O)(O)[O-].[Na+].O1CCCC1>[C:15]([CH:10]([CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1)[C:11]([OH:13])=[O:12])([O:17][CH2:18][CH:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16]

Participants

5

Reactant 2

HCID 270494-(4-Aminophenyl)butanoic acidHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 54758960HCID 54758960, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

4-(4-aminophenyl)butanoic acid (250 mg, 1.4 mmol) in a 10 mL flask was dissolved in a mixture of 10% aqueous sodium bicarbonate (0.29 mL) and tetrahydrofuran (2.1 mL) then cooled in an ice/water bath. 9-fluorenylmethyl chloroformate (390 mg, 1.4 mmol) was added in small portions over 3 min. After 4 h the cooling bath was removed. After additional 4 h at room temperature, the reaction was extracted with deionized water (2 mL) and ethyl ether (2 mL) and the aqueous layer was brought to pH 4 with dilute HCl and placed in a refrigerator. After 1 h solid was collected by vacuum filtration and washed with deionized water then dried under vacuum to give 290 mg of product (52% yield). Mass spectrum C25H23NO4 (M+Na)+ calcd for 424.1. found 424.0.

Workup

  1. temperaturethen cooled in an ice/water bath
  2. customAfter 4 h the cooling bath was removed
  3. extractionthe reaction was extracted with deionized water (2 mL) and ethyl ether (2 mL)
  4. filtrationAfter 1 h solid was collected by vacuum filtration
  5. washwashed with deionized water
  6. customthen dried under vacuum

Sources & evidence

ORD record
ord-170e88f196534d5bb03720641be17a17
Source dataset
uspto-grants-2016_03
Patent number
US09289512B2

Reaction notes

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