2,2-Dimethoxypropane → HCID 68784264, compound

HRID 660387Notes

Reaction equation

HRID 660387 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([CH:34]([CH3:36])[CH3:35])[CH2:11][C@H:12]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C@@H:13]([OH:25])[CH2:14][NH:15][C:16](=[O:24])[C:17]([CH3:23])([CH3:22])[CH2:18][CH2:19][CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:39](OC)([CH3:41])[CH3:40]>CC(C)=O>[CH2:1]([O:8][CH2:9][C@H:10]([CH:34]([CH3:35])[CH3:36])[CH2:11][C@H:12]1[C@@H:13]([CH2:14][NH:15][C:16](=[O:24])[C:17]([CH3:22])([CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])[O:25][C:39]([CH3:41])([CH3:40])[N:26]1[C:27]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 59630981tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate

Product 1

HCID 68784264HCID 68784264, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate (3.8 g, 7.5 mmol) in acetone (50 mL) was added 2,2-dimethoxy-propane (6.0 g, 57.7 mmol). The resulting mixture was cooled to 0° C., BF3Et2O (100 mg, 0.7 mmol) was added. The reaction mixture was allowed to warm to rt and stirred for 2 h. TLC showed the starting material had been consumed. The reaction mixture was quenched with Et3N. The solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The organic layers were washed with H2O and brine, dried over Na2SO4, and evaporated to produce (4S,5R)-tert-butyl 4-((S)-2-(benzyloxymethyl)-3-methylbutyl)-5-((2,2-dimethylhexanamido)methyl)-2,2-dimethyloxazolidine-3-carboxylate (3.0 g, 73%); MS: 547 (M++1).

Workup

  1. additionBF3Et2O (100 mg, 0.7 mmol) was added
  2. temperatureto warm to rt
  3. customhad been consumed
  4. customThe reaction mixture was quenched with Et3N
  5. customThe solvent was removed in vacuo
  6. customthe residue was partitioned between water and EtOAc
  7. washThe organic layers were washed with H2O and brine
  8. dry with materialdried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-c6442da65e1449928fe1856417059ad8
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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