Hydrochloric Acid → 2-(2-(9H-fluoren-9-ylidene)acetamido)acetic acid

HRID 1926183Notes

Reaction equation

HRID 1926183 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][NH:5][C:6](=[O:21])[CH:7]=[C:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.CO.[Li+].[OH-].Cl>O>[CH:10]1[C:9]2[C:8](=[CH:7][C:6]([NH:5][CH2:4][C:3]([OH:22])=[O:2])=[O:21])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 579720572-(2-(9H-fluoren-9-ylidene)acetamido)acetic acid methyl ester

Product 1

HCID 579720622-(2-(9H-fluoren-9-ylidene)acetamido)acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-(9H-fluoren-9-ylidene)acetamido)acetic acid methyl ester (293 mg, 1 mmol) and 300 ml of CH3OH were stirred at room temperature while 25 ml of 4 N solution of LiOH in H2O was added. The mixture was stirred for 5 hours at room temperature. The mixture is neutralized with concentrated hydrochloric acid to pH 7 and evaporated under vacuum to remove methanol. The residue was adjusted to pH 3 with concentrated hydrochloric acid. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (259 mg, 93% yield) as a white solid. LC-MS (m/z) 280 (M+1).

Workup

  1. additionwas added
  2. customevaporated under vacuum
  3. customto remove methanol
  4. filtrationThe solids were collected by vacuum filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6f73e1f539d24033953e20da6c00c701
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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