2,2-Dimethoxypropane → HCID 68614318, compound

HRID 1993126Notes

Reaction equation

HRID 1993126 reaction equation
[OH:1][CH:2]1[CH:8]([OH:9])[CH:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[NH:6][C:5](=[O:18])[NH:4][CH:3]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.CO[C:29](OC)([CH3:31])[CH3:30]>CN(C=O)C>[OH:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH:3]2[NH:4][C:5](=[O:18])[NH:6][CH:7]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)[CH:8]3[CH:2]2[O:1][C:29]([CH3:31])([CH3:30])[O:9]3)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 68613625HCID 68613625, compound

Product 1

HCID 68614318HCID 68614318, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Diol 2.9 (1.8 g, 5.03 mmol) was dissolved in DMF (6 mL) and 2,2-dimethoxypropane (12 mL). P-TsOH (95 mg) was added and the mixture stirred at 65° C. for 3 h. A vacuum was applied to remove water and then the mixture was stirred at 65° C. for a further 1 h. The excess dimethoxypropane was then distilled and the remaining DMF solution was then allowed to cool. The solution of acetonide 2.10 can then used without further purification in future reactions.

Workup

  1. customto remove water
  2. stirringthe mixture was stirred at 65° C. for a further 1 h
  3. distillationThe excess dimethoxypropane was then distilled
  4. temperatureto cool
  5. customThe solution of acetonide 2.10 can then used without further purification in future reactions

Sources & evidence

ORD record
ord-71527cdfb56141e9ad832f9e464a54ba
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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