Hydrochloric Acid → 6-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid

HRID 1926190Notes

Reaction equation

HRID 1926190 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:25])[CH:11]=[C:12]1[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2.CO.[Li+].[OH-].Cl>O>[CH:14]1[C:13]2[C:12](=[CH:11][C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:26])=[O:2])=[O:25])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 425992016-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid methyl ester

Product 1

HCID 574954166-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid methyl ester (349 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 (281 mg, 84% yield) as a white solid. 1H NMR (DMSO-d6) δ1.30 (m, 2H, CH2), 1.51 (m, 4H, 2×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), 8.53 (t, J=4.0 Hz, 1H, CONH), 8.68 (d, J=8.0 Hz, 1H, Ar—H). LC-MS (m/z) 336 (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-cacab5a279154ded9abb1be0f5735e50
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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