Triethylamine → HCID 86744080, compound

HRID 2165273Notes

Reaction equation

HRID 2165273 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([NH:15][C@H:16]1[C@H:19]([CH3:20])[N:18]([OH:21])[C:17]1=[O:22])=[O:14])([CH3:11])([CH3:10])[CH3:9].[C:23]1([CH:29]([O:36][C:37](=[O:40])[CH2:38]Cl)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[C:8]([O:12][C:13]([NH:15][C@H:16]1[C@H:19]([CH3:20])[N:18]([O:21][CH2:38][C:37]([O:36][CH:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:40])[C:17]1=[O:22])=[O:14])([CH3:9])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12946603tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamateHCID 20077950HCID 20077950, compound

Product 1

HCID 86744080HCID 86744080, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0 61 g, 6.0 mmol was dropped into a solution of (3S-trans)-3-(t-butyloxy-carbonylamino)-1-hydroxy-4-methyl-2-azetidinone (1.08 g. 5.0 mmol) and diphenylmethylchloroacetate (1.43 g. 5.5 mmol) in 10 ml of dry dimethylformamide. The mixture was stirred overnight at room temperature. The precipitate was removed by filtration and the solvent was stripped in vacuo. The residue was taken up in ethyl acetate, filtered, washed with 5% NaHCO3 solution and with water, dried over MgSO4 and evaporated in vacuo to give a colorless oil; yield 2.0 g. By storing in a refrigerator the title compound crystallized, melting point 73°-74° C.

Workup

  1. customThe precipitate was removed by filtration
  2. filtrationfiltered
  3. washwashed with 5% NaHCO3 solution and with water
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customto give a colorless oil

Sources & evidence

ORD record
ord-a1ca1a17532e49cb875b88acc3003230
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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