s-Glycerylcysteine → N-Fluorenylmethoxycarbonyl-S-(2,3-dihydroxypropyl)cysteine

HRID 383198

Reaction equation

HRID 383198 reaction equation
[OH:1][CH:2]([CH2:11][OH:12])[CH2:3][S:4][CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])[NH2:7].[C:13]1([CH2:26][O:27][C:28](C2CC(=O)N(O)C2=O)=[O:29])[C:25]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1>C(=O)([O-])[O-].[Na+].[Na+].C(#N)C.O>[C:13]1([CH2:26][O:27][C:28]([NH:7][C@H:6]([C:8]([OH:10])=[O:9])[CH2:5][S:4][CH2:3][CH:2]([OH:1])[CH2:11][OH:12])=[O:29])[C:25]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 15060047s-GlycerylcysteineHCID 21219419fluorenylmethoxycarbonyl-N-hydroxysuccinimide

Product 1

HCID 66831030N-Fluorenylmethoxycarbonyl-S-(2,3-dihydroxypropyl)cysteineYield 63.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

S-(2,3-dihydroxypropyl)cysteine (2.45 g, 12.6 mmole) was dissolved in 9% sodium carbonate (20 ml). A solution of fluorenylmethoxycarbonyl-N-hydroxysuccinimide (3.45 g, 10.5 mmole) in acetonitrile (20 ml) was added and the mixture stirred for 2 h, then diluted with water (240 ml), and extracted with diethyl ether (25 ml×3). The aqueous phase was acidified to pH 2 with concentrated hydrochloric acid and was then extracted with ethyl acetate (70 ml×3). The extract was washed with water (50 ml×2) and saturated sodium chloride solution (50 ml×2), dried over sodium sulfate and evaporated to dryness. Recrystallisation from ether and ethyl acetate at −20° C. yielded a colourless powder (2.8 g, 6.7 mmole, 63.8%).

Workup

  1. extractionextracted with diethyl ether (25 ml×3)
  2. extractionwas then extracted with ethyl acetate (70 ml×3)
  3. washThe extract was washed with water (50 ml×2) and saturated sodium chloride solution (50 ml×2)
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customRecrystallisation from ether and ethyl acetate at −20° C.

Sources & evidence

ORD record
ord-3c987f56724b4e878d2713b95c2e3c80
Source dataset
uspto-grants-2013_02
Patent number
US08367067B2

Linked notes

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