(Dimethyl sulfide)trihydroboron → HCID 18391835, compound

HRID 617762Notes

Reaction equation

HRID 617762 reaction equation
[CH2:1]([C:3]1([CH2:38][CH3:39])[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]([CH3:22])[C:17](=O)[CH2:18][O:19][CH3:20])[CH3:15])=[CH:10][CH:9]=2)[N:5]([C:23]([NH:25][C@H:26]([CH2:34][CH2:35][CH3:36])[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)=[O:24])[C:4]1=[O:37])[CH3:2].B.CSC>C1COCC1>[CH2:38]([C:3]1([CH2:1][CH3:2])[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]([CH2:17][CH2:18][O:19][CH3:20])[CH3:22])[CH3:15])=[CH:10][CH:9]=2)[N:5]([C:23]([NH:25][C@H:26]([CH2:34][CH2:35][CH3:36])[C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)=[O:24])[C:4]1=[O:37])[CH3:39]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 18391857HCID 18391857, compound

Product 1

HCID 18391835HCID 18391835, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (4S)-3,3-diethyl-4-{(S)-4-[1-(N-methoxyacetyl-methylamino)ethyl]phenoxy}-1-[(R)-α-n-propyl-(4-methyl)benzylaminocarbonyl]azetidin-2-one (13 gm, 24 mmol) in THF (150 mL) was added a 2M solution of borane-methyl sulfide in THF (36 mL, 72 nmmol) and the reaction stirred at rt for 7 hrs. The reaction was then quenched with methanol (20 mL) and then dimethylaminoethanol (17 mL) added to decompose the borate complex. After stirring at rt for 16 hrs most of the THF was evaporated in vacuo and the residue was taken up in ether, washed twice with potassium carbonate solution and brine. The aqueous layers were reextracted with another portion of ether and the pooled ether layers were then dried over sodium sulfate and evaporated. The residue was purified by preparative chromatography using 1.5-4% methanol/methylene chloride to afford 11 gm (86%) of the title compound as a viscous oil.

Workup

  1. customThe reaction was then quenched with methanol (20 mL)
  2. additiondimethylaminoethanol (17 mL) added
  3. stirringAfter stirring at rt for 16 hrs most of the THF
  4. customwas evaporated in vacuo
  5. washwashed twice with potassium carbonate solution and brine
  6. dry with materialthe pooled ether layers were then dried over sodium sulfate
  7. customevaporated
  8. customThe residue was purified by preparative chromatography

Sources & evidence

ORD record
ord-7848c392a8fa4055b48f4308512964b1
Source dataset
uspto-grants-1999_09
Patent number
US05952321

Reaction notes

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