2-propyl-1,3-dithiane → HCID 15615041, compound

HRID 620216Notes

Reaction equation

HRID 620216 reaction equation
C([Li])CCC.[CH2:6]([CH:9]1[S:14][CH2:13][CH2:12][CH2:11][S:10]1)[CH2:7][CH3:8].[CH3:15][C:16]([CH3:56])([O:18][C:19]([NH:21][C@H:22]([C:30](N[C@H](C(NC(CC1CCCCC1)C(=O)C(=O)CCC)=O)CC(C)C)=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:20])[CH3:17]>O1CCCC1>[CH:24]1([CH2:23][C@H:22]([NH:21][C:19](=[O:20])[O:18][C:16]([CH3:15])([CH3:17])[CH3:56])[CH:30]([OH:31])[C:9]2([CH2:6][CH2:7][CH3:8])[S:14][CH2:13][CH2:12][CH2:11][S:10]2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 110627072-propyl-1,3-dithianeHCID 70089787HCID 70089787, compoundHCID 178418339Butyllithium

Product 1

HCID 15615041HCID 15615041, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyl lithium (2.5M, 11.76 ml, 29.4 mmol) was added dropwise at -25° to a 40 ml tetrahydrofuran solution of 2-n-propyl-1,3-dithiane from part A (4.536 g, 28.0 mmol). After stirring for 2 hours at -20° to -25°, the solution was cooled to -78° and (S)-<α-[[(1,1-dimethylethoxy)carbonyl]amino]cyclohexanepropanal (3.57 g, 14.0 mmol) was added as a 20 ml tetrahydrofuran solution. A chromatography check after 1 hour revealed the formation of a complex reaction mixture. It was warmed gradually from -78° to -50° over a period of 18 hours, quenched with saturated ammonium chloride (50 ml) and the two layers separated upon warming to room temperature. The aqueous layer was diluted with water (75 ml, to dissolve the precipitated ammonium chloride) and reextracted with ethyl acetate (2×50 ml). Combined organic extracts were washed with saturated ammonium chloride (1×75 ml), dried over anhydrous sodium sulfate and concentrated to give 7.9 g crude product which upon flash chromatographic purification yielded 1.517 g of the title B compound.

Workup

  1. temperaturethe solution was cooled to -78°
  2. waitA chromatography check after 1 hour revealed
  3. customthe formation of a complex reaction mixture
  4. temperatureIt was warmed gradually from -78° to -50° over a period of 18 hours
  5. customquenched with saturated ammonium chloride (50 ml)
  6. customthe two layers separated
  7. additionThe aqueous layer was diluted with water (75 ml
  8. dissolutionto dissolve the precipitated ammonium chloride) and
  9. washCombined organic extracts were washed with saturated ammonium chloride (1×75 ml)
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-749c0fcee0ab497087b0d1fba4eaae61
Source dataset
uspto-grants-1989_04
Patent number
US04820691

Reaction notes

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