Potassium Carbonate → HCID 178454212, compound

HRID 591340Notes

Reaction equation

HRID 591340 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[C@H:37]2[CH2:42][O:41][C@@H:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:39][CH2:38]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[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][C@@H:37]2[CH2:38][O:39][C@@H:40]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[O:41][CH2:42]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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131734514(4S)-N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamateHCID 178427795HCID 178427795, compound

Product 1

HCID 178454212HCID 178454212, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 0.93 g (2 mmol) (4S)—N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate and 1.34 g (4 mmol) cis-2-phenyl-1,3-dioxan-5-yl 4-methylbenzenesulfonate in 18 mL was added potassium carbonate (0.55 g, 4 mmol). The mixture was heated in a microwave for 2 h at 100° C. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to afford 0.165 g (13%) di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-{4-[(trans-2-phenyl-1,3-dioxan-5-yl)oxy]benzyl}-L-glutamate. The benzylidene protected derivative (0.13 g, 0.2 mmoL)) was dissolved in methanol (15 mL) Palladium/C (10% Pd) was added and the mixture was stirred under hydrogen atmosphere over night. The mixture was filtered and the solvent was evaporated, yielding 0.11 g (100%) di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-{4-[(1,3-dihydroxypropan-2-yl)oxy]benzyl}-L-glutamate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-384d5924f3e743afa37c974ef0508e87
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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