Triethylamine → HCID 131721605, compound

HRID 850203Notes

Reaction equation

HRID 850203 reaction equation
O[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].[CH3:17][O:18][C:19](=[O:23])[CH2:20][NH:21][CH3:22].C([N:26](CC)CC)C>CN(C)C=O>[CH3:17][O:18][C:19](=[O:23])[CH2:20][N:21]([NH:26][C:2](=[O:3])[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)[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83545Sarcosine methyl esterHCID 171548Biotin

Product 1

HCID 131721605HCID 131721605, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
12.5 °C

Procedure

To a solution of biotin in anhydrous dimethylformamide is added 1.1 equivalents of N-methylglycine methyl ester and 3 equivalents of triethylamine followed by the addition of 1.05 equivalents of BOP (benzotriazol-1-yloxy-tris (dimethylamine)phosphonium hexafluorophosphate). The mixture is stirred at 0-25° C. for 2-24 h and then concentrated. The residue is diluted with ethyl acetate and the resulting solution is washed with 1 N aqueous hydrochloric acid and then with saturated aqueous sodium bicarbonate. The organic phase is dried over magnesium sulfate, filtered and then concentrated via reduced pressure rotary evaporation. The residue is chromatographed on silica gel, eluting with 5-15% methanol/ethyl acetate. Chromatographic fractions containing product are combined and concentrated to afford the final product (4).

Workup

  1. concentrationconcentrated
  2. additionThe residue is diluted with ethyl acetate
  3. washthe resulting solution is washed with 1 N aqueous hydrochloric acid
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated via reduced pressure rotary evaporation
  7. customThe residue is chromatographed on silica gel
  8. washeluting with 5-15% methanol/ethyl acetate
  9. additionChromatographic fractions containing product
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4dc38148452844be94ad1e0d5eb8743a
Source dataset
uspto-grants-2000_01
Patent number
US06015897

Reaction notes

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