Oxetane, 3-(bromomethyl)-3-methyl- → HCID 69597602, compound

HRID 1796805Notes

Reaction equation

HRID 1796805 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:16]([OH:18])[CH3:17])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cs].Br[CH2:21][C:22]1([CH3:26])[CH2:25][O:24][CH2:23]1>CN(C)C=O>[CH3:21][C:22]1([CH2:26][O:14][C:13](=[O:15])[CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH:16]([OH:18])[CH3:17])[CH2:25][O:24][CH2:23]1

Participants

5

Reactant 3

HCID 144860Oxetane, 3-(bromomethyl)-3-methyl-HCID 433607L-Threonine, N-[(phenylmethoxy)carbonyl]-HCID 5354618Cesium

Product 1

HCID 69597602HCID 69597602, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a N,N-dimethylformamide (750 ml) solution 2-benzyloxycarbonylamino-3-hydroxy-butyric acid, cesium salt (123.9 g, 0.322 mol) at about 23° C. was added 3-bromomethyl-3-methyl-oxetane (60 ml, 0.420 mol). The reaction was stirred at about 23° C. for about 18 hours and was then concentrated in vacuo. The residue was diluted with ethyl acetate and extracted with saturated sodium bicarbonate, washed with saturated ammonium chloride and saturated sodium chloride, dried with sodium sulfate and concentrated to give 100 g of the title compound.

Workup

  1. concentrationwas then concentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. extractionextracted with saturated sodium bicarbonate
  4. washwashed with saturated ammonium chloride and saturated sodium chloride
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d4ccead10a84b02a579ce7df98f679c
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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