Sodium Carbonate → HCID 59279991, compound

HRID 1875383Notes

Reaction equation

HRID 1875383 reaction equation
[Si]([O:8][CH2:9][C:10]([CH3:47])([CH3:46])[CH2:11]/[CH:12]=[CH:13]/[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[C:19]([O:26][CH2:27][CH3:28])[CH:18]=[C:17]2[O:29][C@H:30]1[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:32]([C:42]([O:44][CH3:45])=[O:43])[CH2:31]1)(C(C)(C)C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH2:27]([O:26][C:19]1[CH:18]=[C:17]([O:29][C@H:30]2[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36])[C@H:32]([C:42]([O:44][CH3:45])=[O:43])[CH2:31]2)[C:16]2[C:21](=[CH:22][C:23]([O:24][CH3:25])=[C:14](/[CH:13]=[CH:12]/[CH2:11][C:10]([CH3:47])([CH3:46])[CH2:9][OH:8])[CH:15]=2)[N:20]=1)[CH3:28]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 59279957HCID 59279957, compound

Product 1

HCID 59279991HCID 59279991, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(HF)3-Et3N (523 mL, 3210 mmol) was added to a solution of the product from Step 2 (54 g, 80 mmol) in THF (802 mL) at 0° C. The mixture was then warmed to RT. After 15 hours, the solvent was removed in vacuo, and the residue was taken up in EtOAc (500 mL) and water (450 mL). Na2CO3 (553 g, 5216 mmol) then was added slowly. The solution then stirred 15 minutes, and the organic layer was then extracted with 10% NaHCO3 (1×) and brine (1×) and dried over MgSO4; and the solvent was removed in vacuo. The original aqueous layer was back-extracted with EtOAc and combined with the first extraction. The crude material was then purified on silica (gradient elution, 0-80% EtOAc/hexane) to yield of the title compound. LRMS ESI+ (M+H)+ 559.3, calcd for C30H43N2O8: 559.3.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionthe organic layer was then extracted with 10% NaHCO3 (1×) and brine (1×)
  3. dry with materialdried over MgSO4
  4. customand the solvent was removed in vacuo
  5. extractionThe original aqueous layer was back-extracted with EtOAc
  6. extractioncombined with the first extraction
  7. customThe crude material was then purified on silica (gradient elution, 0-80% EtOAc/hexane) to yield of the title compound

Sources & evidence

ORD record
ord-d14c9b26a2f248029726265454dfcebc
Source dataset
uspto-grants-2012_11
Patent number
US08309540B2

Reaction notes

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