tert-Butyl bromoacetate → HCID 15908942, compound

HRID 480585Notes

Reaction equation

HRID 480585 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[NH2:10][CH2:11][C@@H:12]([OH:14])[CH3:13].C(N(C(C)C)CC)(C)C.C(Cl)Cl.CO>CN(C)C=O>[OH:14][C@@H:12]([CH3:13])[CH2:11][NH:10][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 21226129Dichloromethane methanol

Product 1

HCID 15908942HCID 15908942, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.91 ml of tert-butyl bromoacetate is added dropwise within 30 minutes to a mixture of 15.00 g of (S)-(+)-1-amino-2-propanol and 6.97 ml of diisopropylethylamine in 100 ml of N,N-dimethylformamide, while cooling with an ice bath. Then the cooling bath is removed and the reaction mixture is stirred overnight at ambient temperature. For working up, the solvent is distilled off in vacuo, the flask residue is dissolved in 50 ml water and saturated with 15 g of sodium chloride. The aqueous phase is extracted several times with ethyl acetate. The extracts are combined, washed with 20 ml of saturated sodium chloride solution, dried over magnesium sulfate, and concentrated by evaporation. The oily yellowish crude product is reacted further without any more purification. Yield: 7.80 g (103% of theory); Rf value: 0.42 (silica gel, methylene chloride/methanol=9:1); mass spectrum (ESI+): m/z=190 [M+H]+.

Workup

  1. temperaturewhile cooling with an ice bath
  2. customThen the cooling bath is removed
  3. distillationthe solvent is distilled off in vacuo
  4. dissolutionthe flask residue is dissolved in 50 ml water and saturated with 15 g of sodium chloride
  5. extractionThe aqueous phase is extracted several times with ethyl acetate
  6. washwashed with 20 ml of saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated by evaporation
  9. customThe oily yellowish crude product is reacted further without any more purification

Sources & evidence

ORD record
ord-9be55aea513b48e7ae96c518b66a52c3
Source dataset
uspto-grants-2003_11
Patent number
US06653305B2

Reaction notes

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