Hydrochloric Acid → 8-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid

HRID 1926205Notes

Reaction equation

HRID 1926205 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:27])[CH:13]=[C:14]1[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2.CO.[Li+].[OH-].Cl>O>[CH:16]1[C:15]2[C:14](=[CH:13][C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:28])=[O:2])=[O:27])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 579720548-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid methyl ester

Product 1

HCID 579720638-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid methyl ester (377 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 (345 mg, 95% yield) as a white solid. 1H NMR (DMSO-d6) δ1.23 (m, 2H, CH2), 1.45 (m, 6H, 3×CH2), 1.49 (m, 2H, CH2), 2.18 (t, J=8.0 Hz, 2H, CH2CO), 3.23 (m, 2H, NCH2), 7.08 (s, 1H, ═CH—CO), 7.34 (m, 2H, Ar—H), 7.41 (t, J=8.0 Hz, 2H, Ar—H), 7.76 (d, J=8.0 Hz, 1H, Ar—H), 7.81 (m, 2H, Ar—H), 8.50 (t, J=4.0 Hz, 1H, CONH), 8.67 (d, J=8.0 Hz, 1H, Ar—H). LC-MS (m/z) 364 (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-4dd5cd8c6a904368a519f5032c559e21
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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