4-Aminophenylacetic acid → HCID 56923945, compound

HRID 926816Notes

Reaction equation

HRID 926816 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.Cl[C:13]([O:15][CH2:16][CH:17]1[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14]>C(=O)(O)[O-].[Na+].O1CCCC1>[C:13]([CH:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)[C:9]([OH:11])=[O:10])([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14]

Participants

5

Reactant 2

HCID 145334-Aminophenylacetic acidHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 56923945HCID 56923945, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

4-aminophenyl acetic acid (204 mg, 1.35 mmol) in a 10 mL flask was dissolved in a mixture of 10% aqueous sodium bicarbonate (0.29 mL) and tetrahydrofuran (2.3 mL) then cooled in an ice/water bath. 9-fluorenylmethyl chloroformate (367 mg, 1.42 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 284 mg of product (56% yield). Mass spectrum (M+Na)+ calcd for C23H19NO4, 396.1. found, 396.1.

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-0aee40c5493c4e73b64b3cf6fe8691be
Source dataset
uspto-grants-2016_03
Patent number
US09289512B2

Reaction notes

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