Acetic Acid → HCID 69238679, compound

HRID 1522318Notes

Reaction equation

HRID 1522318 reaction equation
[H-].[Na+].CCO.[C:6]([O:10][C:11]([NH:13][C@H:14]([C:23]([O:25]CC)=O)[CH2:15][S:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(O)(=O)C>CCCCC.C1COCC1>[CH2:21]([O:20][C:18]([C@H:17]1[C:23](=[O:25])[CH:14]([NH:13][C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH2:15][S:16]1)=[O:19])[CH3:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 24758Sodium hydrideHCID 7072232HCID 7072232, compound

Product 1

HCID 69238679HCID 69238679, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

NaH (1.64 g, 55%-65% Fluka, 41 mmole) washed with pentane twice, was suspended in THF (20 mL), then EtOH anhydrous (2.4 mL, 41 mmole) was added slowly. When the production of H2 stopped, more THF (160 mL) was added and followed by 12 (13.73 g, 41 mmole) in THF (20 mL). After 40 min. acetic acid 4 mL was added. The solvent was removed under vacuum. The crude product was extracted with diethylether and washed with brine. Crude (12 g) was flash chromatographied (column diam. 7.5 cm, SiO2 15 cm high), elution with cyclohexane-ethylacetate (4/1) to give 9.22 g of 13 (yield 78%).

Workup

  1. customThe solvent was removed under vacuum
  2. extractionThe crude product was extracted with diethylether
  3. washwashed with brine
  4. wash(column diam. 7.5 cm, SiO2 15 cm high), elution with cyclohexane-ethylacetate (4/1)

Sources & evidence

ORD record
ord-4dbdd45a939e48d1bbd3b43b2c723f89
Source dataset
uspto-grants-2015_07
Patent number
US09073966B2

Reaction notes

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