Water → (S)-2-tert-butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid methyl ester

HRID 2270822Notes

Reaction equation

HRID 2270822 reaction equation
[CH3:1][C:2]([CH3:31])([O:4][C:5]([NH:7][C@H:8]([C:28]([OH:30])=[O:29])[CH2:9][NH:10][C:11]([O:13][CH2:14][CH:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])=[O:6])[CH3:3].[C:32](=O)([O-])O.[K+].IC.O>CN(C)C=O>[CH3:3][C:2]([CH3:31])([O:4][C:5]([NH:7][C@H:8]([C:28]([O:30][CH3:32])=[O:29])[CH2:9][NH:10][C:11]([O:13][CH2:14][CH:15]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:12])=[O:6])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 516893Potassium BicarbonateHCID 7019527(2S)-2-(((tert-butoxy)carbonyl)amino)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoic acid

Product 1

HCID 59977282(S)-2-tert-butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid methyl esterYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-[(1,1-dimethylethoxy)carbonyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine (5.00 g, 11.7 mmol) in N,N-dimethylformamide (10 mL) was treated with potassium hydrogen carbonate (1.4 g, 14.1 mmol) and iodomethane (0.8 ml, 12.9 mmol). The reaction mixture was stirred at room temperature for 2 h. Then water was added and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4), concentrated and chromatographed (10-40% ethyl acetate/hexanes) to give N-[(1,1-dimethylethoxy)carbonyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester (4.20 g, 81%) as a white solid.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed (10-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2189d8fa306d4afead2f15136e4264e5
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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