Pyridine → HCID 88753232, compound

HRID 414166Notes

Reaction equation

HRID 414166 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].C([N:19]([CH2:22][CH3:23])CC)C.C([O:26]C(Cl)=O)C.N1C=CC=CC=1.C[N:37](C)[CH:38]=[O:39]>CCOCC>[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:8]1[C:16]([NH2:15])=[CH:11][C:10]2[C:38]([NH:37][NH:19][C:22](=[O:26])[C:23]=2[CH:7]=1)=[O:39]

Participants

7

Reactant 5

HCID 1049PyridineHCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 171548Biotin

Product 1

HCID 88753232HCID 88753232, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

Biotin (0.29 g, 1.2 mmole) and 0.17 ml triethylamine were dissolved in 20 ml dry dimethylformamide under anhydrous conditions and cooled to -10° C. A solution of 0.141 ml ethylchloroformate in 2.86 ml ether was added slowly and the reaction was stirred for 30 min. A precipitate which formed was separated by filtration. A suspension consisting of 600 mg (2.4 mmole) of the intermediate from Part C, 20 ml dry dimethylformamide and 1 ml dry pyridine was added to the filtrate quickly. This mixture was stirred at -10° C. for 30 min and then at room temperature overnight. During this period a solution was obtained. The dimethylformamide was removed by distillation at 60° C. and 0.10 mm Hg pressure. The oily residue was stirred with 50 ml 0.1N hydrochloric acid for 1 hr. A white solid which formed was filtered and washed with 0.1N hydrochloric acid and then water. After drying under a vacuum at room temperature overnight, 0.55 g (97% yield) of the product was obtained, m.p. 170°-3° C. Calculated for C21H28N6O5S: C, 52.92; H, 5.92; N, 17.64. Found: C, 51.69; H, 5.90; N, 17.63.

Workup

  1. customA precipitate which formed
  2. customwas separated by filtration
  3. additionwas added to the filtrate quickly
  4. stirringThis mixture was stirred at -10° C. for 30 min
  5. customat room temperature
  6. customovernight
  7. customDuring this period a solution was obtained
  8. customThe dimethylformamide was removed by distillation at 60° C.
  9. stirringThe oily residue was stirred with 50 ml 0.1N hydrochloric acid for 1 hr
  10. customA white solid which formed
  11. filtrationwas filtered
  12. washwashed with 0.1N hydrochloric acid
  13. customAfter drying under a vacuum at room temperature overnight

Sources & evidence

ORD record
ord-f3842af19a3b4f3e8998b5998e500849
Source dataset
uspto-grants-1988_12
Patent number
US04791055

Reaction notes

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