Sodium Bicarbonate → HCID 54172520, compound

HRID 343647Notes

Reaction equation

HRID 343647 reaction equation
[CH3:1][N:2]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@@H:3]([CH2:10][S:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4](N(C)OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])O.[Na+]>C(OCC)C.O>[CH3:1][N:2]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:3]([CH:4]=[O:5])[CH2:10][S:11][C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 22941573HCID 22941573, compound

Product 1

HCID 54172520HCID 54172520, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-35 °C

Procedure

4.2 g of N-(-N-methyl-2(R)-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionyl)-N,O-dimethylhydroxylamine in 15 cm3 of diethyl ether are added, at a temperature in the region of -45° C., to a suspension of 0.386 g of lithium aluminium hydride in 35 cm3 of diethyl ether. The temperature is allowed, with stirring, to rise to approximately 0° C. After cooling to a temperature in the region of -35° C., a solution of 1.77 g of sodium hydrogen carbonate in 6.5 cm3 of water is added. The organic phase is washed 3 times with 10 cm3 of a normal hydrochloric acid solution, then twice with 10 cm3 of a saturated sodium hydrogen carbonate solution and finally with 10 cm3 of a saturated sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure. 2.2 g of N-methyl-N-tert-butoxycarbonyl-S-(triphenylmethyl)cysteinal are obtained, which are used in the following stage without other purification.

Workup

  1. customto rise to approximately 0° C
  2. washThe organic phase is washed 3 times with 10 cm3 of a normal hydrochloric acid solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a668b992abe4b40b84214a2c162d47c
Source dataset
uspto-grants-1999_01
Patent number
US05861529

Reaction notes

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