Dimethyl Sulfoxide → tert-Butyl amino(oxo)acetate

HRID 1071372Notes

Reaction equation

HRID 1071372 reaction equation
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=[O:7].C(Cl)Cl.C(NO)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O.C([N:25](CC)CC)C>C(Cl)Cl.C1COCC1>[C:6]([C:5]([NH2:25])=[O:9])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:7]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 12453830tert-Butyl amino(oxo)acetateYield 85%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

DMSO (6.3 mL, 88 mmol) was added dropwise to a 2M solution of oxalyl chloride in CH2Cl2 (24.3 mL, 48.6 mmol) at −78° C. After 15 min, amino alcohol 22a (9.6 g, 44 mmol) in 80 mL CH2Cl2/THF (1:1) was added dropwise followed by dropwise addition of triethylamine (30.8 mL, 220 mmol) The reaction mixture was warmed to rt and stirred for 2. The reaction mixture was partitioned between EtOAc and sat KH2PO4, separated, and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated by rotary evaporator. The residue was purified by silica gel chromatography to give 8.0 g (85% yield) of Boc-amino ketone 22b.

Workup

  1. customThe reaction mixture was partitioned between EtOAc
  2. customseparated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporator
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cca30010941a46b7910c49017641301e
Source dataset
uspto-grants-2005_06
Patent number
US06906053B2

Reaction notes

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