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

HRID 393050Notes

Reaction equation

HRID 393050 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-8c140f68cc4e430096068e1391d1a6c2
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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