Potassium Sodium Tartrate → tert-Butyl [(2R)-1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

HRID 1796849Notes

Reaction equation

HRID 1796849 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14](O)=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].COCCO[Al+]OCCOC.[Na+].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[OH:15][CH2:14][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11][S:12][CH3:13]

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 111051N-(tert-Butyloxycarbonyl)-D-methionineHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 44593821tert-Butyl [(2R)-1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamateYield 76.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-(tert-butoxycarbonyl)-D-methionine (12.47 g, 50 mmol) and sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al®) (50 mmol) in dry toluene (125 mL) was stirred at 0° C. for 30 minutes, then at ambient temperature for 1 hour. The mixture was treated with aqueous Rochelle salt and extracted with diethyl ether. The extract was washed sequentially with brine and aqueous NaHCO3, dried (MgSO4), filtered, and concentrated to provide the desired product (9.05 g).

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed sequentially with brine and aqueous NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-290b7772ca7f43a3b498863d26f957ea
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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