Hydrochloric Acid → 5-(2-(9H-fluoren-9-ylidene)acetamido)pentanoic acid

HRID 1926187Notes

Reaction equation

HRID 1926187 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:24])[CH:10]=[C:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2.CO.[Li+].[OH-].Cl>O>[CH:13]1[C:12]2[C:11](=[CH:10][C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:25])=[O:2])=[O:24])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 579720535-(2-(9H-fluoren-9-ylidene)acetamido)pentanoic acid methyl ester

Product 1

HCID 579720655-(2-(9H-fluoren-9-ylidene)acetamido)pentanoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(2-(9H-fluoren-9-ylidene)acetamido)pentanoic acid methyl ester (335 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 24 hours at room temperature. The mixture was 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 (279 mg, 87% yield) as a white solid. LC-MS (m/z) 322 (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-b8e01ae05cd14242aac6a10c61d42710
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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