Dimethylformamide → HCID 86738864, compound

HRID 414160Notes

Reaction equation

HRID 414160 reaction equation
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].C1(N=C=NC2CCCCC2)CCCCC1.CN(C)C=[O:35]>>[OH:3][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:1].[CH:11]1[C:16]([OH:35])=[CH:8][C:7]2[O:3][C:2]([CH:4]=[CH:5][C:6]=2[CH:10]=1)=[O:1]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10868Dicyclohexylcarbodiimide2×HCID 171548Biotin

Product 1

HCID 86738864HCID 86738864, compound

Conditions

Temperature
7 °C

Procedure

A reaction mixture was formed by dissolving in 10 ml of dimethylformamide 100 mg of unbelliferone, 167 mg of biotin, and 141 mg of dicyclohexyl carbodiimide. The reaction mixture was incubated at -18° C. for about 4 hours, then overnight at 7° C. and allowed to stand at room temperature for from 3 to 4 hours. An additional 141 mg of dicyclohexylcarbodiimide was added and the reaction mixture was stirred at 7° C. for from 3 to 4 hours and allowed to stand at room temperature overnight. The resulting precipitate was filtered off and discarded. To the filtrate was added 75 ml of ice water, and the resulting mixture was incubated at 0° C. for 1 hour. The precipitate which resulted was filtered off and discarded. The filtrate was evaporated to dryness and the residue dissolved in from 3 to 4 ml of methylene chloride. To the resulting solution was added 5 ml of diethylether. The resulting precipitate which comprised the biotin-umbelligerone conjugate was filtered off, dried, and stored at room temperature.

Workup

  1. customA reaction mixture was formed
  2. customovernight
  3. customat 7° C.
  4. customto stand at room temperature for from 3 to 4 hours
  5. waitto stand at room temperature overnight
  6. filtrationThe resulting precipitate was filtered off
  7. additionTo the filtrate was added 75 ml of ice water
  8. waitthe resulting mixture was incubated at 0° C. for 1 hour
  9. customThe precipitate which resulted
  10. filtrationwas filtered off
  11. customThe filtrate was evaporated to dryness
  12. dissolutionthe residue dissolved in from 3 to 4 ml of methylene chloride
  13. additionTo the resulting solution was added 5 ml of diethylether
  14. filtrationwas filtered off
  15. customdried
  16. customstored at room temperature

Sources & evidence

ORD record
ord-f5ee5fcc5ff44c938fe500a4095321ba
Source dataset
uspto-grants-1988_12
Patent number
US04791055

Reaction notes

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