Triethylamine → HCID 86626203, compound

HRID 2355507Notes

Reaction equation

HRID 2355507 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@:8]([C@@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([NH:23][C@@H:24]([CH2:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:25][N:26]([CH3:36])[C:27]([O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])=[O:28])=[O:22])[CH2:16]2)([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@:8]([C@@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([NH:23][C@@H:24]([CH2:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:25][N:26]([CH3:36])[C:27]([O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:35])[CH3:34])=[O:28])=[O:22])[CH2:16]2)([OH:14])[CH2:9][CH2:10][CH2:11][CH:12]=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 67191221HCID 67191221, compound

Product 1

HCID 86626203HCID 86626203, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A 100 mL, round-bottom flask was charged with (3R)-3-((S)-1-(3-chlorophenyl)-1,5-dihydroxypentyl)-N—((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propan-2-yl)piperidine-1-carboxamide (0.0544 g (0.0852 mmol), DMSO (2.5 mL) and Et3N (1 mL). The flask was cooled in an ice bath and a mixture of pyridine-sulphur trioxide complex (0.24 g, 1.51 mmol) and dry DMSO (2.5 mL) was added. After 10 min, the ice bath was removed. The reaction mixture was allowed to stir at rt for 3 h. The mixture was quenched with brine, extracted with EtOAc (3×) and dried over Na2SO4. Removal of the solvent left crude (3R)-3-((S)-1-(3-chlorophenyl)-4-formyl-1-hydroxybutyl)-N—((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)piperidine-1-carboxamide (0.1036 g), which was carried on to the next step without further purification. LC-MS (3 min) tR=2.43 min, m/z 658, 660 (MNa+), 636 (MH+), 618, 620.

Workup

  1. temperatureThe flask was cooled in an ice bath
  2. additionwas added
  3. customthe ice bath was removed
  4. customThe mixture was quenched with brine
  5. extractionextracted with EtOAc (3×)
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent
  8. waitleft crude (3R)-3-((S)-1-(3-chlorophenyl)-4-formyl-1-hydroxybutyl)-N—((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)piperidine-1-carboxamide (0.1036 g), which
  9. customwas carried on to the next step without further purification
  10. customLC-MS (3 min) tR=2.43 min, m/z 658, 660 (MNa+), 636 (MH+), 618, 620

Sources & evidence

ORD record
ord-a789e1b020864405b00a6350461382ed
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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