Triethylamine → HCID 14581286, compound

HRID 982514Notes

Reaction equation

HRID 982514 reaction equation
[CH3:1][N:2]([CH3:25])[C@H:3]1[C:9](=[O:10])[N:8]2[C@@H:4]1[CH2:5][C:6](=O)[C@@H:7]2[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:12].C(N(CC)CC)C.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[C:48]([NH:51][CH2:52][CH2:53][SH:54])(=[O:50])[CH3:49]>CN(C)C=O.C(OCC)(=O)C>[C:48]([NH:51][CH2:52][CH2:53][S:54][C:6]1[CH2:5][C@H:4]2[N:8]([C:9](=[O:10])[C@@H:3]2[N:2]([CH3:1])[CH3:25])[C:7]=1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)=[O:12])(=[O:50])[CH3:49]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 14484AcetylcysteamineHCID 73910Diphenylphosphinic chlorideHCID 14581284HCID 14581284, compound

Product 1

HCID 14581286HCID 14581286, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-35 °C

Procedure

69 mg (0.21 mmol) of p-nitrobenzyl (2R,5R,6R)-6-dimethylamino-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate [34] was dissolved in 1.5 ml of dimethylformamide. The solution was cooled to -35° C., and 45 microliters (0.32 mmol) of triethylamine and 58 microliters (0.28 mmol) of diphenylphosphoryl chloride was added, and the mixture was reacted at the above temperature for 30 minutes. The progress of the reaction was determined by the formation of a spot showing a UV absorption at an Rf of 0.46 in silica gel TLC developed with ethyl acetate, and the subsequent reaction was carried out. Specifically, 0.5 ml of a dimethylformamide solution of 54 microliters (0.38 mmol) of triethylamine and 46 mg (0.38 mmol) of N-acetylcysteamine was gradually added dropwise to the reaction mixture at -35° C. The reaction was carried out at the same temperature for 30 minutes. The reaction mixture was poured into 50 ml of ethyl acetate, and washed with 30 ml of 0.1M phosphate buffer (pH 8.9) and 20 ml of a saturated aqueous solution of sodium chloride. The washings were again extracted with ethyl acetate and washed with a saturated aqueous solution of sodium chloride. The extracts were combined, and dried over anhydrous sodium sulfate. The dried product was concentrated under reduced pressure to remove the solvent and 26 mg of crystals of the captioned compound were collected by filtration. The mother liquor was dried under reduced pressure, and dissolved in methylene chloride. The solution was adsorbed on a column of silica gel (7 g). The column was eluted with ethyl acetate, acetone and ethyl acetate/methanol (2/1). Those fractions in the eluates which had a UV absorption at an Rf of 0.15 in silca gel TLC developed with acetone were collected and dried under reduce pressure to give 49 mg (yield 83%) of the captioned compound.

Workup

  1. customthe mixture was reacted at the above temperature for 30 minutes
  2. customa UV absorption at an Rf of 0.46 in silica gel TLC
  3. customthe subsequent reaction
  4. washwashed with 30 ml of 0.1M phosphate buffer (pH 8.9) and 20 ml of a saturated aqueous solution of sodium chloride
  5. extractionThe washings were again extracted with ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe dried product was concentrated under reduced pressure
  9. customto remove the solvent and 26 mg of crystals of the captioned compound
  10. filtrationwere collected by filtration
  11. customThe mother liquor was dried under reduced pressure
  12. dissolutiondissolved in methylene chloride
  13. washThe column was eluted with ethyl acetate, acetone and ethyl acetate/methanol (2/1)
  14. customa UV absorption at an Rf of 0.15 in silca gel TLC
  15. customwere collected
  16. customdried

Sources & evidence

ORD record
ord-54071a00c47d4492bd7cd516ed2840f8
Source dataset
uspto-grants-1991_02
Patent number
US04996314

Reaction notes

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