Sodium Bicarbonate → HCID 70871763, compound

HRID 470703Notes

Reaction equation

HRID 470703 reaction equation
[NH2:1][CH2:2][C@H:3]1[O:8][CH2:7][C@H:6]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][CH2:4]1.[C:17]([O:20][CH2:21][CH:22]=O)(=[O:19])[CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[C:17]([O:20][CH2:21][CH2:22][NH:1][CH2:2][C@H:3]1[O:8][CH2:7][C@H:6]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][CH2:4]1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 111159952-oxoethyl acetateHCID 68311107HCID 68311107, compound

Product 1

HCID 70871763HCID 70871763, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound (500 mg, 2.17 mmol) obtained in Step 3 above was dissolved in dichloromethane (10 ml), 2-oxoethyl acetate (243 mg, 2.39 mmol) was added and the resulting mixture was stirred at room temperature for 1 hour. Then sodium triacetoxyborohydride (920 mg, 4.34 mmol) was added and the resulting mixture was stirred at room temperature for 3 hours. After reaction, saturated sodium bicarbonate solution (50 ml) was added and the resulting mixture was further stirred for 1 hour. The reaction mixture was diluted with dichloromethane and the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue obtained was purified by silica gel column chromatography [chloroform:methanol=40:1→20:1 (v/v)] to give 544 mg (64%) of the title compound as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. additionwas added
  3. stirringthe resulting mixture was further stirred for 1 hour
  4. washthe organic layer was washed with brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography [chloroform:methanol=40:1→20:1 (v/v)]

Sources & evidence

ORD record
ord-d8f7de5f13c34990aa8a5717c7b5b271
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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