Water → Benzyloxycarbonyl-L-homocystine

HRID 1768433Notes

Reaction equation

HRID 1768433 reaction equation
[CH2:1]([S:8][S:9][CH2:10][CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=[O:14])[CH2:2][C@H:3]([NH2:7])[C:4]([OH:6])=[O:5].[OH-].[Na+].[CH2:19]([O:26][C:27](Cl)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>O1CCOCC1.O.O1CCOCC1>[CH2:19]([O:26][C:27]([CH:1]([S:8][S:9][CH2:10][CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=[O:14])[CH2:2][C@H:3]([NH2:7])[C:4]([OH:6])=[O:5])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 439579L-Homocystine

Product 1

HCID 86605612Benzyloxycarbonyl-L-homocystine

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

L-homocystine (5 g) was dissolved in a mixture (80 ml) of dioxane/H2O. At 0° C. and under stirring, 1.52 g (2.1 eq) of NaOH and a solution of 7.8 g (2.4 eq) of benzylchloroformate in 40 ml dioxane were added. The pH was maintained at 9 by addition of a solution of NaOH 1M. After stirring for 2.30 h at room temperature, 100 ml H2O were added and the white precipitate was extracted by Et20 (2×50 ml). The aqueous phase was acidified to pH 1 and the precipitate was extracted by EtOAc (4×80 ml). The organic phase was washed, dried over Na2SO4, filtered and evaporated in vacuo. White solid 10.2 g (100%).

Workup

  1. stirringAfter stirring for 2.30 h at room temperature
  2. extractionthe white precipitate was extracted by Et20 (2×50 ml)
  3. extractionthe precipitate was extracted by EtOAc (4×80 ml)
  4. washThe organic phase was washed
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb52912f54cd4fa4a4f0c42d9cdadace
Source dataset
uspto-grants-2007_06
Patent number
US07235687B2

Reaction notes

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