Triethylamine → Biotin-2,3,5,6-tetrafluorophenyl ester

HRID 433848Notes

Reaction equation

HRID 433848 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(CC)CC)C.FC(F)(F)C(O[C:29]1[C:34]([F:35])=[C:33]([F:36])[CH:32]=[C:31]([F:37])[C:30]=1[F:38])=O>CN(C=O)C>[F:35][C:34]1[C:33]([F:36])=[CH:32][C:31]([F:37])=[C:30]([F:38])[C:29]=1[O: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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 171548BiotinHCID 153342582,3,5,6-Tetrafluorophenyl trifluoroacetate

Product 1

HCID 20610690Biotin-2,3,5,6-tetrafluorophenyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 2.5 g (10.3 mmol) quantity of d-biotin in 20 mL anhydrous DMF under argon atmosphere was warmed to 60° C. with stirring to effect dissolution. 1.7 mL (12.5 mmol) triethylamine was added, followed by 3.4 g (12.5 mmol) 1. The mixture was stirred for 2 hours, after which the solvent was removed by rotary evaporation. The resultant semi-solid was triturated with 15 mL ether twice to produce a white solid (2.6 g, 65%). 1H-NMR. (Ref. Wilbur, D. S., Bioconj. Chem., v8 pp572-584)

Workup

  1. dissolutiondissolution
  2. stirringThe mixture was stirred for 2 hours
  3. customafter which the solvent was removed by rotary evaporation
  4. customThe resultant semi-solid was triturated with 15 mL ether twice

Sources & evidence

ORD record
ord-6251ad13041e49b1a1563a85b608e9db
Source dataset
uspto-grants-2003_12
Patent number
US06670194B1

Reaction notes

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