Potassium Carbonate → Di-tert-butyl (4S)-N-(tert-butoxvcarbonyl)-4-[4-({2-phenyl-5-[(tosyloxy)methyl]-1,3-dioxan-5-yl}methoxy)benzyl]-L-glutamate

HRID 591285Notes

Reaction equation

HRID 591285 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([O:50][CH2:51][C:52]2([CH2:64]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:57][O:56][CH:55]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[O:54][CH2:53]2)(=[O:49])=[O:48])=[CH:43][CH:42]=1>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:64][C:52]2([CH2:51][O:50][S:47]([C:44]3[CH:43]=[CH:42][C:41]([CH3:40])=[CH:46][CH:45]=3)(=[O:48])=[O:49])[CH2:57][O:56][CH:55]([C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)[O:54][CH2:53]2)=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12458135(2-Phenyl-1,3-dioxane-5,5-diyl)bis(methylene) bis(4-methylbenzenesulfonate)HCID 70957078di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate

Product 1

HCID 89136260Di-tert-butyl (4S)-N-(tert-butoxvcarbonyl)-4-[4-({2-phenyl-5-[(tosyloxy)methyl]-1,3-dioxan-5-yl}methoxy)benzyl]-L-glutamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 466 mg (1.0 mmol) of di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate in 12 mL N,N-dimethylformamide were added 138 mg (1.0 mmol) of potassium carbonate and 533 mg (1.0 mmol) of (2-phenyl-1,3-dioxane-5,5-diyl)bis(methylene) bis(4-methylbenzenesulfonate) (Heterocycles 34. (1992), 739), and the resulting suspension was heated for 2 h at 100° C. in a microwave oven. The reaction mixture was then filtered, the solvent evaporated and the residue was taken up in ethyl acetate and water. The organic phase was separated off, washed with water until neutral, dried over sodium sulfate and filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel using a dichloromethane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customthe solvent evaporated
  3. customThe organic phase was separated off
  4. washwashed with water until neutral,
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was chromatographed on silica gel using a dichloromethane/ethyl acetate gradient
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0babea73b7054cd5b2eb3c64b5aaa7a9
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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