Formic Acid → HCID 118093718, compound

HRID 625709Notes

Reaction equation

HRID 625709 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH2:12][CH2:13][C:14]3=[O:19])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)=O.C(N(CC)CC)C.O>C(Cl)Cl>[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH2:12][CH2:13][C@@H:14]3[OH:19])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 8471TriethylamineHCID 15723443HCID 15723443, compound

Product 1

HCID 118093718HCID 118093718, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen a solution of the material from Step 2 (0.39 g) in CH2Cl2 (10 mL) is added dropwise to a stirred mixture of formic acid (0.20 mL) and triethylamine (0.61 mL) with cooling in an ice-bath. Chloro([1S,2S)-(−)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido)(mesitylene)ruthenium(II) (26 mg) is added and the reaction mixture stirred at 0° C. for 3 hours. Water is added and the resulting mixture extracted twice with ethyl acetate. The combined organic layers are washed (saturated aqueous NaHCO3), dried and purified by column chromatography (silica gel, cyclohexane:ethyl acetate gradient 100:0 to 50:50), to obtain the desired material (0.39 g). LC (METHOD 14): tR=0.83 min; Mass spectrum: m/z=257 [M+H−H2O]+.

Workup

  1. temperaturewith cooling in an ice-bath
  2. extractionthe resulting mixture extracted twice with ethyl acetate
  3. washThe combined organic layers are washed (saturated aqueous NaHCO3)
  4. customdried
  5. custompurified by column chromatography (silica gel, cyclohexane:ethyl acetate gradient 100:0 to 50:50)

Sources & evidence

ORD record
ord-d72683b122b14c51affed6b1d34b0378
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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