Acetone → HCID 86612808, compound

HRID 643240Notes

Reaction equation

HRID 643240 reaction equation
BrCC(O[CH2:6][CH2:7][CH2:8][O:9][C:10](=[O:13])[CH2:11][Br:12])=O.[CH2:14]([C@H:29]([NH2:33])[C:30]([OH:32])=[O:31])[CH2:15][C:16]([NH:18][C@H:19]([C:22]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:23])[CH2:20][SH:21])=[O:17].[OH-:34].[Na+].C[C:37]([CH3:39])=[O:38]>O>[Br:12][CH2:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:39][C:37]([O:34][S:21][CH2:20][C@@H:19]([C:22]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:23])[NH:18][C:16](=[O:17])[CH2:15][CH2:14][C@@H:29]([C:30]([OH:32])=[O:31])[NH2:33])=[O:38])=[O:13]

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 124886GlutathioneHCID 44154035Propane-1,3-diyl bis(bromoacetate)

Product 1

HCID 86612808HCID 86612808, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of bromoacetic acid 3-(2-bromoacetoxy)propyl ester (1.05 g, 3.29 mmol) in 18 ml of acetone was slowly added an aqueous, out-gassed solution of GSH (0.2 g, 0.65° mmol) in 10 ml H2O containing 1 molar equivalent of NaOH. The mixture was allowed to stir at room temperature for 3 h. The mixture was washed with CHCl3 (4×60 ml). Aqueous layer was decanted from the organic layer and the solvent was removed from the aqueous layer in vacuo. The glassy residue was purified by reverse-phase HPLC (Waters μBondapak C18, 7.8×300 mm) using a running solvent composed of H2O:MeOH:acetic acid (80:20:1, v/v/v). Yield: 18%. 1H NMR 300 MHz (D2O, ref HOD (δ 4.8)) δ 3.931 (2H, s, —C(O)CH2Br), 2.045 (2H, p, J=6.4 Hz —OCH2CH2—), 4.247 (2H, t, J=3.9 Hz, —SCH2C(O)OCH2CH2—), 4.227 (2H, t, J=3.9 Hz, BrCH2C(O)OCH2CH2—), 4.015 (2H, s, Gly-CH2), 3.412 (2H, s, —SCH2C(O)O), 2.920 (1H, q, J=14.7, 9.0 Hz, —CCHxHyS—), 3.122 (1H, q, J=14.7, 5.2 Hz, —CCHxHyS—), 4.581 (1H, q, J=14.1, 6.0 Hz, Cys-CH), 2.136 (2H, t, J=7.2, 7.2 Hz, -Glu-CβH2), 2.511 (2H, t, J=7.2, 7.2 Hz, -Glu-CγH2), 3.775 (1H, t, J=6.0, 6.0 Hz, -Glu-CαH).

Workup

  1. washThe mixture was washed with CHCl3 (4×60 ml)
  2. customAqueous layer was decanted from the organic layer
  3. customthe solvent was removed from the aqueous layer in vacuo
  4. customThe glassy residue was purified by reverse-phase HPLC (Waters μBondapak C18, 7.8×300 mm)

Sources & evidence

ORD record
ord-69dffdcba0aa4213a488ac8f267e82fc
Source dataset
uspto-grants-2010_04
Patent number
US07700560B2

Reaction notes

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