Sodium Hydroxide → beta-Cyclodextrin

HRID 2059538Notes

Reaction equation

HRID 2059538 reaction equation
[CH2:1]([OH:77])[C@H:2]1[O:7][C@@H:6]2[O:8][C@H:9]3[C@H:14]([OH:15])[C@@H:13]([OH:16])[C@@H:12]([O:17][C@H:18]4[C@H:23]([OH:24])[C@@H:22]([OH:25])[C@@H:21]([O:26][C@H:27]5[C@H:32]([OH:33])[C@@H:31]([OH:34])[C@@H:30]([O:35][C@H:36]6[C@H:41]([OH:42])[C@@H:40]([OH:43])[C@@H:39]([O:44][C@H:45]7[C@H:50]([OH:51])[C@@H:49]([OH:52])[C@@H:48]([O:53][C@H:54]8[C@H:60]([OH:61])[C@@H:59]([OH:62])[C@@H:57]([O:58][C@H:3]1[C@H:4]([OH:76])[C@H:5]2[OH:75])[O:56][C@@H:55]8[CH2:63][OH:64])[O:47][C@@H:46]7[CH2:65][OH:66])[O:38][C@@H:37]6[CH2:67][OH:68])[O:29][C@@H:28]5[CH2:69][OH:70])[O:20][C@@H:19]4[CH2:71][OH:72])[O:11][C@@H:10]3[CH2:73][OH:74].CC(OOC(C)(C)C)(C)C.N[C@H](C(O)=O)CCC(=O)OCC1C=CC=CC=1.C(=O)(O)[O-].[Na+].N(C(OCC1C=CC=CC=1)=O)[C@H](C(ON1C(=O)CCC1=O)=O)CCC(=O)OCC1C=CC=CC=1.[OH-].[Na+]>O.C1COCC1.CC#N>[CH2:67]([OH:68])[C@H:37]1[O:38][C@@H:39]2[O:44][C@H:45]3[C@H:50]([OH:51])[C@@H:49]([OH:52])[C@@H:48]([O:53][C@H:54]4[C@H:60]([OH:61])[C@@H:59]([OH:62])[C@@H:57]([O:58][C@H:3]5[C@H:4]([OH:76])[C@@H:5]([OH:75])[C@@H:6]([O:8][C@H:9]6[C@H:14]([OH:15])[C@@H:13]([OH:16])[C@@H:12]([O:17][C@H:18]7[C@H:23]([OH:24])[C@@H:22]([OH:25])[C@@H:21]([O:26][C@H:27]8[C@H:32]([OH:33])[C@@H:31]([OH:34])[C@@H:30]([O:35][C@H:36]1[C@H:41]([OH:42])[C@H:40]2[OH:43])[O:29][C@@H:28]8[CH2:69][OH:70])[O:20][C@@H:19]7[CH2:71][OH:72])[O:11][C@@H:10]6[CH2:73][OH:74])[O:7][C@@H:2]5[CH2:1][OH:77])[O:56][C@@H:55]4[CH2:63][OH:64])[O:47][C@@H:46]3[CH2:65][OH:66]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 122337L-Glutamic acid, 5-(phenylmethyl) esterHCID 516892Sodium BicarbonateHCID 15228398Z-Glu(obzl)-osuHCID 131725389beta-cyclodextrin DTBP

Product 1

HCID 444041beta-Cyclodextrin

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Synthesis of H-Glu-Glu-Adamantane 7. H-Glu(Bn)-OH (3.55 g, 15 mmol) was dissolved in water (16 mL) containing sodium bicarbonate (1.26 g, 15 mmol). To the mixture was added Z-Glu(Bn)-OSu (4.68 g, 10 mmol) in THF (30 mL). To the mixture was added another 30 mL THF, 20 mL CH3CN and then 2N NaOH 10 mL. The solution was stirred for 16 hours at room temperature. THF and CH3CN was evaporated under high vacuum. To the aqueous mixture was added 1 N HCl to adjust the pH to 3. Precipitation was observed. The mixture was extracted with chloroform (3×30 mL). The organic phase was dried with MgSO4. MgSO4 was removed by filtration. Organic solvent was evaporated to give white sticky solid 6. 6 was used for next step reaction without further purification.

Workup

  1. customTHF and CH3CN was evaporated under high vacuum
  2. additionTo the aqueous mixture was added 1 N HCl
  3. customPrecipitation
  4. extractionThe mixture was extracted with chloroform (3×30 mL)
  5. dry with materialThe organic phase was dried with MgSO4
  6. customMgSO4 was removed by filtration
  7. customOrganic solvent was evaporated

Sources & evidence

ORD record
ord-28c1be4d65b042db92f7e8dd54e9046d
Source dataset
uspto-grants-2012_10
Patent number
US08277846B2

Reaction notes

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