Triethylamine → HCID 86626203, compound

HRID 1254390Notes

Reaction equation

HRID 1254390 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-58047a5e21944c50b7e20fab25ebfafc
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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