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

HRID 1275785Notes

Reaction equation

HRID 1275785 reaction equation
C[O:2][C:3](=[O:28])[C@H:4]([CH2:7][O:8][C:9]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:5][CH3:6].[OH-].[Na+]>CO>[CH3:6][NH:5][C@H:4]([C:3]([OH:28])=[O:2])[CH2:7][O:8][C:9]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53855539N-Methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

Product 1

HCID 9863641N-methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.032 g (0.085 mmol) N-methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester from Step 1 in methanol (1 mL) was added 20% sodium hydroxide (1 mL) and the mixture stirred at room temperature for 1 h. Most of the ethanol was evaporated under vacuo, the residue suspended in water (5 mL) nd extracted with diethyl ether (2×1 mL). The alkaline aqueous phase was acidified with 20% acetic acid by cooling with an ice bath, the white precipitate was filtered, washed with water and dried in vacuo over P2O5 to give 0.027 g (yield 90%) N-methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine as a white powder.

Workup

  1. customMost of the ethanol was evaporated under vacuo
  2. extractionextracted with diethyl ether (2×1 mL)
  3. temperatureby cooling with an ice bath
  4. filtrationthe white precipitate was filtered
  5. washwashed with water
  6. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-fbacc8944c7a43f591b1909f281b6496
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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