Sodium Hydroxide → HCID 131722495, compound

HRID 324163Notes

Reaction equation

HRID 324163 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][N:5]([NH:7][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[C@@H:21]2[C@@H:16]([NH:17][C:18]([NH:20]2)=[O:19])[CH2:15][S:14]1)[CH3:6].[OH-].[Na+]>CO>[C:8]([NH:7][N:5]([CH3:6])[CH2:4][C:3]([OH:23])=[O:2])(=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[C@@H:21]2[C@@H:16]([NH:17][C:18]([NH:20]2)=[O:19])[CH2:15][S:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131721605HCID 131721605, compound

Product 1

HCID 131722495HCID 131722495, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of biotinamido-N-methyl-glycine methyl ester in methanol is added 1.5-2.0 equivalents of 1 N aqueous sodium hydroxide. The mixture is stirred at 15-45° C. for 4-24 h and then concentrated via reduced pressure rotary evaporation. The residue is diluted with deionized water and the pH of the solution is adjusted to 1-2 by addition of 6 N aqueous hydrochloric acid. The mixture is again concentrated via reduced pressure rotary evaporation. The residue is chromatographed on reverse phase C-18 silica gel, and eluted with methanol/water. The fractions containing the product are combined and concentrated to afford the final product (5).

Workup

  1. concentrationconcentrated via reduced pressure rotary evaporation
  2. additionThe residue is diluted with deionized water
  3. additionthe pH of the solution is adjusted to 1-2 by addition of 6 N aqueous hydrochloric acid
  4. concentrationThe mixture is again concentrated via reduced pressure rotary evaporation
  5. customThe residue is chromatographed on reverse phase C-18 silica gel
  6. washeluted with methanol/water
  7. additionThe fractions containing the product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d89607b93f9b4a8d8722448c8a546cd4
Source dataset
uspto-grants-2001_04
Patent number
US06217869B1

Reaction notes

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