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

HRID 1275787Notes

Reaction equation

HRID 1275787 reaction equation
C[O:2][C:3](=[O:29])[C@H:4]([CH2:8][O:9][C:10]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:5]([CH3:7])[CH3:6].[OH-].[Na+]>CO>[CH3:6][N:5]([CH3:7])[C@H:4]([C:3]([OH:29])=[O:2])[CH2:8][O:9][C:10]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54462480N,N-dimethyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

Product 1

HCID 9929447N,N-dimethyl-O-(9-phenyl-9H-fluoren-9-yl)-L-serineYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.39 g (1 mmol) N,N-Dimethyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester from Step 1 in methanol (4 mL) was added 20% sodium hydroxide (2 mL) and the mixture stirred at room temperature for 1 h. Most of the methanol was evaporated in vacuo, the residue suspended in water (10 mL) and extracted with diethyl ether (2×2 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 0.314 g (yield 84%) N,N-dimethyl-O-(9-phenyl-9H-fluoren-9-yl)-L-serine as a white powder. 1H NMR (CD3OD, 300 MHz) δ: 7.87 (br s, 2H), 7.70-7.10 (m, 11H), 3.70-3.45 (m, 3H), 2.95 (s, 6H).

Workup

  1. customMost of the methanol was evaporated in vacuo
  2. extractionextracted with diethyl ether (2×2 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-d77c7d41737045f2b7a78335d84ac190
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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