Triethylamine → HCID 56634376, compound

HRID 2165277Notes

Reaction equation

HRID 2165277 reaction equation
[OH:1][N:2]1[C@@H:5]([CH3:6])[C@H:4]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:3]1=[O:15].Br[CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C(N(CC)CC)C>CN(C)C=O>[C:11]([O:10][C:8]([NH:7][C@H:4]1[C@H:5]([CH3:6])[N:2]([O:1][CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C:3]1=[O:15])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62576Benzyl bromoacetateHCID 12946603tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamate

Product 1

HCID 56634376HCID 56634376, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3S-trans)-1-Hydroxy-3-[(t-butyloxycarbonyl)-amino]-4-methyl-2-azetidinone (21.6g) was dissolved in 300ml of dimethylformamide, 25.2g of bromoacetic acid. phenylmethyl ester was added. 17 ml of triethylamine was added. and the mixture was stirred for 3 hours at room temperature. The resulting precipitate was filtered off. The filtrate evaporated in vacuo, the residue dissolved in ethyl acetate and the solution treated with water, the pH of which was adjusted to 7. The organic phase was washed twice with water, dried (MgSO4) and evaporated to yield 33.4g of the title compound as an oil.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customThe filtrate evaporated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. additionthe solution treated with water
  5. washThe organic phase was washed twice with water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-23fb2373c58d474097439292d160949d
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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