Water → di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-{[(4S,5S)-2,2-dimethyl-5-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,3-dioxolan-4-yl]methoxy}benzyl)-L-glutamate

HRID 591339Notes

Reaction equation

HRID 591339 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:23]([O-:25])=[O:24])[CH2:10][C@H:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:12]([O-:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S(O[CH2:37][C@H:38]2[C@H:42]([CH2:43][O:44][S:45]([C:48]3[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=3)(=[O:47])=[O:46])[O:41][C:40]([CH3:56])([CH3:55])[O:39]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:23]([O:25][C:11]([CH3:15])([CH3:12])[CH3:10])=[O:24])[CH2:10][C@H:11]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:37][C@H:38]2[C@H:42]([CH2:43][O:44][S:45]([C:48]3[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=3)(=[O:47])=[O:46])[O:41][C:40]([CH3:56])([CH3:55])[O:39]2)=[CH:20][CH:21]=1)[C:12]([O:14][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 974391,3-Dioxolane-4,5-dimethanol, 2,2-dimethyl-, 4,5-bis(4-methylbenzenesulfonate), (4S,5S)-HCID 131734514(4S)-N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate

Product 1

HCID 117812720di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-{[(4S,5S)-2,2-dimethyl-5-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,3-dioxolan-4-yl]methoxy}benzyl)-L-glutamateYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 0.47 g (1 mmol) (4S)—N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate and 0.47 g (1 mmol) [(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl bis(4-methylbenzenesulfonate) in 15 mL DMF was added potassium carbonate (0.28 g, 2 mmol). The mixture was heated in a microwave for 2 h at 100° C. Water was added and the mixture was extracted with dichloromethane. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (silica, 20% ethyl acetate in hexane) to afford 0.25 g (33%) di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-(4-{[(4S,5S)-2,2-dimethyl-5-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,3-dioxolan-4-yl]methoxy}benzyl)-L-glutamate.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (silica, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-215891f86d9c461da36554d175abefb0
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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