Methanol → s-Glycerylcysteine

HRID 876097

Reaction equation

HRID 876097 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C@H:10]([C:13]([OH:15])=[O:14])[CH2:11][SH:12].Br[CH2:17][CH:18]([OH:21])[CH2:19][OH:20].CO>O.CC(C)=O>[OH:21][CH:18]([CH2:19][OH:20])[CH2:17][S:12][CH2:11][C@@H:10]([C:13]([OH:15])=[O:14])[NH2:9]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 208273-Bromo-1,2-propanediolHCID 60960Cysteine Hydrochloride

Product 1

HCID 15060047s-Glycerylcysteine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Triethylamine (6 g, 8.2 ml, 58 mmoles) was added to L-cysteine hydrochloride (3 g, 19 mmole) and 3-bromo-propan-1,2-diol (4.2 g, 2.36 ml, 27 mmole) in water and the homogeneous solution kept at room temperature for 3 days. The solution was reduced in vacuo at 40° C. to a white residue which was boiled with methanol (100 ml), centrifuged and the residue dissolved in water (5 ml). This aqueous solution was added to acetone (300 ml) and the precipitate isolated by centrifugation. The precipitate was purified by several precipitations from water with acetone to give S-(2,3-dihydroxypropyl)cysteine as a white amorphous powder (2.4 g, 12.3 mmol, 64.7%).

Workup

  1. customwas reduced in vacuo at 40° C. to a white residue which
  2. customthe precipitate isolated by centrifugation
  3. customThe precipitate was purified by several precipitations from water with acetone

Sources & evidence

ORD record
ord-8abb0f3045ab46498ee78a8d015f1766
Source dataset
uspto-grants-2015_03
Patent number
US08986700B2

Linked notes

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