Formic Acid → HCID 90027005, compound

HRID 1506992Notes

Reaction equation

HRID 1506992 reaction equation
C(#N)C.Cl[S:5]([N:8]=C=O)(=[O:7])=[O:6].C(O)=O.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C@H:21]1[O:25][C:24]([CH3:27])([CH3:26])[O:23][C@@H:22]1[CH2:28][OH:29].CN(C)C(=O)C>>[S:5](=[O:6])(=[O:7])([O:29][CH2:28][C@@H:22]1[C@@H:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[Cl:14])[O:25][C:24]([CH3:27])([CH3:26])[O:23]1)[NH2:8]

Participants

6

Reactant 5

HCID 284Formic AcidHCID 6342AcetonitrileHCID 31374DimethylacetamideHCID 70918Chlorosulfonyl isocyanateHCID 90028018HCID 90028018, compound

Product 1

HCID 90027005HCID 90027005, compoundYield 72.3%

Conditions

Temperature
0 °C

Procedure

To a 100 ml flask, Acetonitrile (2.26 ml, 43.2 mmol) was added and cooled to 0° C. Chlorosulfonyl isocyanate (1.5 ml, 17.3 mmol), and formic acid (0.65 ml, 17.3 mmol) was added dropwise and stirred at room temperature for 6 hours. ((4R,5R)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (Preparation example 6, 1.05 g, 4.3 mmol) in N,N-dimethyl acetamide (13.2 ml, 142.7 mmol) was slowly added at 0° C. and stirred at room temperature for 1 hours. The reaction mixture was quenched with H2O, extracted with EtOAc, and washed with H2O. The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated. The crude compound was purified by a silica gel column to produce the title compound (1.00 g, 50˜80%).

Workup

  1. stirringstirred at room temperature for 1 hours
  2. customThe reaction mixture was quenched with H2O
  3. extractionextracted with EtOAc
  4. washwashed with H2O
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-601bf6f592544073871c285b2c64cba2
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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