Dimethyl Sulfoxide → HCID 18470943, compound

HRID 567797Notes

Reaction equation

HRID 567797 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C:19](=[O:31])[NH:20][CH2:21][CH:22]([OH:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[O:30]=[C:22]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:21][NH:20][C:19](=[O:31])[O:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18470931HCID 18470931, compound

Product 1

HCID 18470943HCID 18470943, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

Dry DMSO (3.0 ml, 43.54 mmol) in CH2Cl2 (6.9 ml) was added dropwise to a solution of oxalyl chloride (1.73 ml, 19.91 mmol) in CH2Cl2 (35 ml) at −60° C. under a nitrogen atmosphere. After stirring for 2 mins at −60° C. a solution of (RS)-benzyl-N-(2-hydroxy-3-phenylpropyl)carbamate (preparation 1) (5.18 g, 18.15 mmol) in CH2Cl2 (17 ml) was added dropwise over 10 mins followed by triethylamine (17.63 ml, 90.74 mmol). The resultant mixture was allowed to warm to room temperature, whereupon water (100 ml) was added. The aqueous mixture was extracted with CH2Cl2 (3×100 ml) and the combined organic extracts washed with sat aq brine (2×250 ml) and dried over MgSO4. Filtration away from the drying agent followed by evaporation of the solvent gave the crude product which was purified by chromatography (SiO2; eluting with 40:60 hexane:ethyl acetate) to give the desired product (yellow crystalline solid, 4.41 g, 86%). 1H NMR (CDCl3) δ:3.72 (s, 2H), 4.11 (d, 2H), 5.09 (s, 2H), 5.45 (s, br, 1H), 7.20-7.37 (m, 10H). LRMS m/z=301.0 (M+18)+.

Workup

  1. additionwas added dropwise over 10 mins
  2. additionwas added
  3. extractionThe aqueous mixture was extracted with CH2Cl2 (3×100 ml)
  4. washthe combined organic extracts washed with sat aq brine (2×250 ml)
  5. dry with materialdried over MgSO4
  6. filtrationFiltration away from the drying agent
  7. customfollowed by evaporation of the solvent
  8. customgave the crude product which
  9. customwas purified by chromatography (SiO2; eluting with 40:60 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-6a1a116c03294ce6ad2c9f9d2557e8e3
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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