Dimethyl Sulfoxide → HCID 86706199, compound

HRID 529466Notes

Reaction equation

HRID 529466 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:61])[C@@H:19]([NH:43][C:44](=[O:60])[O:45][CH2:46][CH:47]1[C:59]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:53]2[C:48]1=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:20]([CH3:42])([S:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:21]>C(Cl)Cl>[CH3:42][C:20]([S:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:21])[C@H:19]([NH:43][C:44](=[O:60])[O:45][CH2:46][CH:47]1[C:59]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:53]2[C:48]1=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:18](=[O:61])[NH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[O:11]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 68292892HCID 68292892, compound

Product 1

HCID 86706199HCID 86706199, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a round bottom dry flask was added DCM (2 mL), and a 2 M solution of oxalyl chloride in DCM (0.100 mL, 0.200 mmol). The reaction was cooled to −78° C. Then slowly was DMSO (0.028 mL, 0.401 mmol) added over 5 min. The reaction was stirred at −78° C. for 30 min. Then (R)-(9H-fluoren-9-yl)methyl 1-(5-hydroxypentylamino)-3-methyl-1-oxo-3-(tritylthio)butan-2-ylcarbamate (100 mg, 0.143 mmol) in DCM (3 mL) was added to the reaction over 5 min and the reaction was stirred at −78° C. for 45 min. Then TEA (0.088 mL, 0.630 mmol) was added to the reaction and the reaction was stirred for additional 30 min at −35° C. The reaction was quenched with EtOAc (2 mL). The reaction was diluted with EtOAc (20 mL) and washed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and saturated aqueous NaCl (10 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give (R)-(9H-fluoren-9-yl)methyl 3-methyl-1-oxo-1-(5-oxopentylamino)-3-(tritylthio)butan-2-ylcarbamate (95 mg, 0.14 mmol, 95% yield).

Workup

  1. stirringthe reaction was stirred at −78° C. for 45 min
  2. stirringthe reaction was stirred for additional 30 min at −35° C
  3. customThe reaction was quenched with EtOAc (2 mL)
  4. additionThe reaction was diluted with EtOAc (20 mL)
  5. washwashed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and saturated aqueous NaCl (10 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b210adcb6ef34a66adb1480197b44369
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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