Potassium Hydroxide → HCID 53731832, compound

HRID 1603656Notes

Reaction equation

HRID 1603656 reaction equation
[CH2:1]([S:8][C@H:9]1[NH:12][C:11](=[O:13])[C@@H:10]1[Br:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:31])[CH2:29]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[K+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:31])[CH2:29][N:12]2[C@H:9]([S:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@H:10]([Br:14])[C:11]2=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 2723671Tetrabutylammonium HydroxideHCID 19605306HCID 19605306, compoundHCID 54383686HCID 54383686, compound

Product 1

HCID 53731832HCID 53731832, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3S, 4R)-4-benzylthio-3-bromoazetidin-2-one (0.7 g, 2.6 mmol) in dry THF (25 ml) was treated with N-(6-phenylhexyl)bromoacetamide (0.8 g, 2.6 mmol), powdered potassium hydroxide (0.2 g 3 mmol) and tetrabutylammonium hydroxide (0.1 g, 0.3 mmol). The mixture was stirred at room temperature for 4 h and partitioned between ether and brine. The organic layer was separated, dried (MgSO4) and evaporated. The residue was purified by flash chromatography using 3:1 ether:pentane as the eluting solvent. Evaporation of the appropriate fractions gave the title compound as an oil (0.63 g, 53%). 1H NMR δ (CDCl3) 1.21-1.66 (8H, m, (CH2)4), 2.59 (2H, t, J=7.4 Hz, CH2), 3.48,3.82 (each 1H, d, J=16 Hz, NCH2), 3.21 (2H, h, J=6.00 Hz, CH2), 3.37 (1H, dd, J=5.15 Hz, H3b), 3.83 (2H, s, SCH2), 4.59 (1H, d, J=1.6 Hz, H4), 4.89 (1H, d, J=1.6 Hz, H3), 6.04 (1H, bt, NH), 7.14-7.36 (10H, m, Ph--H).

Workup

  1. custompartitioned between ether and brine
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-b51b8f356b6b4f479311bff0f0a3b728
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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