Sodium Hydroxide → 4-(4-{[(9H-fluoren-9-yl)methoxy]carbonyl}piperazin-1-yl)benzoic acid

HRID 478619Notes

Reaction equation

HRID 478619 reaction equation
Cl.[N:2]1([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[OH-].[Na+].[C:19](Cl)([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20].C(N(C(C)C)CC)(C)C>O1CCOCC1.O>[C:19]([N:5]1[CH2:4][CH2:3][N:2]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)([O:21][CH2:22][CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[C:35]1=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:20]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 343679-Fluorenylmethyl chloroformateHCID 81531DiisopropylethylamineHCID 168761224-(Piperazin-1-yl)benzoic acid hydrochloride

Product 1

HCID 180024674-(4-{[(9H-fluoren-9-yl)methoxy]carbonyl}piperazin-1-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent3×

Procedure

4-Piperazin-1-yl-benzoic acid hydrochlorid (10.5 mmol) is dissolved in 15 ml Dioxan and 11.6 ml NaOH (2N) and cooled to 0° C. Simultaneously, FMOC-chloride (11.6 mmol) in dioxan (5 ml) and diisopropyl-ethylamine (11.6 mmol) in dioxan (5 ml) are added dropwise over 20 minutes at 0° C. and the mixture is stirred for 15 minutes and is then allowed to warm up to rt and is stirred over night. The mixture is diluted with water (50 ml) and extracted 2 times with diethylether. The water phase is acidified with aqueous HCl (4N) at 0-4° C. and the solid material formed is filtered off, washed with water and dried (vacuum). A white powder with Rf=0.2 (CH2Cl2/MeOH =95:5) is obtained.

Workup

  1. stirringis stirred over night
  2. extractionextracted 2 times with diethylether
  3. customis acidified with aqueous HCl (4N) at 0-4° C.
  4. customthe solid material formed
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried (vacuum)
  8. customA white powder with Rf=0.2 (CH2Cl2/MeOH =95:5) is obtained

Sources & evidence

ORD record
ord-00024c4d1a1e472783902e7e88893b42
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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