Hydrochloric Acid → 4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid

HRID 2381040Notes

Reaction equation

HRID 2381040 reaction equation
P([O-])([O-])([O-])=O.[OH-].[Na+].[Na+].[Cl-].C[C@@H]([C@@H]1[C@@]2(C)[C@@H](O)C[C@@H]3[C@@]4(C)CC[C@@H](O)C[C@H]4C[C@@H](O)[C@H]3[C@@H]2CC1)C[CH2:13][C:14]([NH:16][CH2:17][CH2:18][S:19]([O-:22])(=[O:21])=[O:20])=O.[Na+].[CH2:46]1[N:51](CCS(O)(=O)=O)[CH2:50][CH2:49][O:48][CH2:47]1.Cl.CC1C(C)=C(OC(CCC(OCCO)=O)=O)C(C)=C2CCC(CCCC(CCCC(CCCC(C)C)C)C)(C)OC=12.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>O.C(Cl)(Cl)Cl>[CH2:46]1[N:51]([CH2:50][CH2:49][OH:48])[CH2:13][CH2:14][N:16]([CH2:17][CH2:18][S:19]([OH:22])(=[O:20])=[O:21])[CH2:47]1

Participants

11

Reactant 8

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 5234Sodium Chloride2×HCID 14798Sodium Hydroxide2×HCID 714062-Hydroxyethyl 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-yl butanedioateHCID 781654-Morpholineethanesulfonic acid2×HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 23666345Sodium Taurocholate2×

Product 1

HCID 238314-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

FaSSIF (Fasted State Simulated Intestinal Fluid) was prepared based on blank FaSSIF which is a phosphate buffer obtained by dissolving 0.696 g NaOH (BDH Laboratory Supplies, Poole, England), 7.908 g NaH2PO4.H2O (Merck, Darmstadt, Germany) and 12.37 g NaCl in 2 L of purified water (18.2 MΩ, Elga, Tex., USA). The pH was adjusted to exactly 6.5 with 1M NaOH. FaSSIF was created by adding 3.23 g sodium taurocholate (ICN Biomedicals, Eschwege, Germany) and 5.9 mL of a solution of lecithin (YDS Chemicals, Heusden, Belgium) in chloroform (100 mg·mL−1) to approximately 200 mL blank FaSSIF. This mixture was heated to 80° C. for 15 minutes to remove all chloroform, after which a clear solution was obtained. Subsequently, blank FaSSIF was added up to a volume of 11. Some experiments were performed with MES buffered FaSSIF to allow the addition of SGF (simulated gastric fluid, 0.1M HCl containing 0.2 wt. % NaCl) without a significant pH change. MES [2-(N-morpholino)-ethanesulfonic acid, Sigma-Aldrich, Steinheim, Germany] (977.3 mg), sodium taurocholate (179.1 mg) and lecithin solution (655.6 μl) were added to prepare 100 ml of MES-FaSSIF according to the same protocol as mentioned before. As receiver medium for the Caco-2 transport experiments, 0.2 wt. % TPGS (D-α-tocopherol polyethylene glycol 1000 succinate, Eastman, Anglesey, England) in transport medium (TM) [HBSS (Hanks' Balanced Salt Solution) supplemented with glucose (to obtain a final concentration of 25 mM, Sigma-Aldrich, Steinheim, Germany) and Hepes-buffer (10 mM, pH 7.4, N-2-hydroxyethyl-piperazine-N′-2-ethanesulfonic acid, Lonza, Verviers, Belgium)] was used. To maintain sink conditions, TPGS was included in the medium added to the basolateral side of the Caco-2 cell monolayer.

Workup

  1. customFaSSIF (Fasted State Simulated Intestinal Fluid) was prepared
  2. customobtained
  3. customto remove all chloroform
  4. customafter which a clear solution was obtained
  5. customto prepare 100 ml of MES-FaSSIF according to the same protocol

Sources & evidence

ORD record
ord-4ea3f2b3fb864918a3a1814e6a732dbb
Source dataset
uspto-grants-2012_09
Patent number
US08258137B2

Reaction notes

Loading…