Sodium Thiosulfate → tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamate

HRID 1244077Notes

Reaction equation

HRID 1244077 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]([CH3:13])([CH3:12])[CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]([CH3:13])([CH3:12])[CH2:9][CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 15473340tert-Butyl (4-hydroxy-2-methylbutan-2-yl)carbamate

Product 1

HCID 11788901tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamateYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(3-Hydroxy-1,1-dimethyl-propyl)-carbamic acid tert-butyl ester (6.0 g, 30 mmol) was dissolved in CH2Cl2 (50 mL) and treated with Dess-Martin periodinane (20.0 g, 44 mmol). After stirring overnight 50 mL of water was added followed by NaHCO3 and Na2S2O3. The resultant mixture was stirred vigorously for 30 min and then was extracted with CH2Cl2 (3–50 mL). The extracts were dried with MgSO4 and concentrated to give 3.26 g (54%) of an orange oil. This material was used in the next step without purification.

Workup

  1. additionwas added
  2. extractionwas extracted with CH2Cl2 (3–50 mL)
  3. dry with materialThe extracts were dried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4244d101663441eba5a280cd1b3b3ff8
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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