Sodium Hydroxide → O-(9-phenyl-9H-fluoren-9-yl)-L-serine

HRID 1275751Notes

Reaction equation

HRID 1275751 reaction equation
C[O:2][C:3](=[O:27])[C@H:4]([CH2:6][O:7][C:8]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH2:5].[OH-].[Na+]>CO>[C:21]1([C:8]2([O:7][CH2:6][C@@H:4]([C:3]([OH:27])=[O:2])[NH2:5])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]3[C:20]2=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15516030O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

Product 1

HCID 9819560O-(9-phenyl-9H-fluoren-9-yl)-L-serineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6.4 g (17.8 mmol) of O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester from step 2 in methanol (20 mL) was added 20% sodium hydroxide (10 mL) and the mixture stirred at room temperature for 1 h. Most of the methanol was evaporated under vacuo, the residue suspended in water (200 mL) and extracted with diethyl ether (2×50 mL). The alkaline aqueous phase was added dropwise into 20% acetic acid (30 mL) with stirring and cooling with an ice bath, the white precipitate was filtered, washed with water and dried in vacuo over P2O5 to give 5.3 g (yield 90%) of O-(9-phenyl-9H-fluoren-9-yl)-L-serine as a white powder. 13C NMR (DMSO-d6, 75 MHz) δ: 167.0, 146.4, 146.1, 143.3, 140.3, 140.0, 129.4, 129.2, 128.4, 128.2, 128.0, 127.2, 125.6, 125.5, 125.1, 120.5, 120.4, 88.4, 63.2, 54.8.

Workup

  1. customMost of the methanol was evaporated under vacuo
  2. extractionextracted with diethyl ether (2×50 mL)
  3. additionThe alkaline aqueous phase was added dropwise into 20% acetic acid (30 mL)
  4. stirringwith stirring
  5. temperaturecooling with an ice bath
  6. filtrationthe white precipitate was filtered
  7. washwashed with water
  8. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-954781d0247c451a894558eb601e0fa5
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

Loading…