Hydrochloric Acid → HCID 88139793, compound

HRID 1954062Notes

Reaction equation

HRID 1954062 reaction equation
[NH2:1][CH:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][SH:5].[OH-].[Na+].Br[CH:12](C)[CH2:13][OH:14].Cl.N[C@H:18](C(O)=O)C(S)(C)C.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>C(O)C.O1CCOCC1.O>[CH3:18][C@@:2]([C:6]([OH:8])=[O:7])([CH2:3][CH2:4][SH:5])[N:1]([CH2:12][CH2:13][OH:14])[S:41]([C:38]1[CH:39]=[CH:40][C:35]([O:34][CH3:33])=[CH:36][CH:37]=1)(=[O:43])=[O:42]

Participants

11

Reactant 7

HCID 313Hydrochloric Acid2×HCID 778(+-)-HomocysteineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 117132-Bromopropan-1-olHCID 14798Sodium HydroxideHCID 92863L-Penicillamine

Product 1

HCID 88139793HCID 88139793, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

D,L-Homocysteine (6.0 g, 44.3 mmol) in 2N NaOH (28.8 mL, 57.7 mmol, 1.3 equiv) is stirred at 0° C. under an argon atmosphere. A solution of 2-bromopropanol (6.66 g, 53.3 mol, 1.2 equiv) in ethanol (50 mL) is slowly added dropwise at 0° C. The resulting solution is stirred overnight at room temperature and then the mixture is acidified to pH~6 with 1 N HCl. The solvent is removed under reduced pressure to leave a thick oil. The penicillamine adduct is then dissolved in dioxane (100 mL) and water (100 mL) and stirred at room temperature. Triethylamine (13.5 g, 133.2 mmol, 3 equiv) is then added to the reaction mixture followed by 4-methoxyphenylsulfonyl chloride (10.0 g, 48.8 mmol, 1.1 equiv). The resulting homogeneous solution is stirred at room temperature for 18 hours and then acidified to pH~2 with 1N HCl. The solution is poured into water and extracted with methylene chloride. The organic extracts were dried (MgSO4) and concentrated to an oil under reduced pressure. The resulting oil is diluted in methanol (30 mL) and enough diazomethane in diethyl ether is added to form a yellow solution. The mixture is concentrated under reduced pressure to leave a colorless oil. Purification of the resulting methyl ester is accomplished by chromatography on silica gel using 1/1 hexane/EtOAc as the eluent. The desired product is obtained as a clear, colorless oil. MS (ESI): 364 (M+H+), 381 (M+NH4+).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customto leave a thick oil
  3. stirringThe resulting homogeneous solution is stirred at room temperature for 18 hours
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. concentrationconcentrated to an oil under reduced pressure
  7. additionThe resulting oil is diluted in methanol (30 mL)
  8. additionenough diazomethane in diethyl ether is added
  9. customto form a yellow solution
  10. concentrationThe mixture is concentrated under reduced pressure
  11. customto leave a colorless oil
  12. customPurification of the resulting methyl ester

Sources & evidence

ORD record
ord-9bd28fbf30ac41fcb45bd82873ff1699
Source dataset
uspto-grants-2000_09
Patent number
US06121258

Reaction notes

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