Formic Acid → HCID 89524608, compound

HRID 1621021Notes

Reaction equation

HRID 1621021 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:8].C(N(CC)CC)C.C(O)=O>C([O-])(O)=O.[Na+]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]([C:9]1([C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:17][CH:18]=2)[CH2:12][CH2:11][CH2:10]1)[OH:8]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 66748116HCID 66748116, compound

Product 1

HCID 89524608HCID 89524608, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of Example 288B (6.63 g, 20.64 mmol), triethylamine (7.19 ml, 51.6 mmol), formic acid (3.40 ml, 89 mmol), and (S,S)—N-(p-touenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cumene)ruthenium (II) (0.131 g, 0.206 mmol) was heated at 35° C. for 16 hours. The reaction mixture was cooled, diluted with saturated NaHCO3 solution, and extracted twice with CH2Cl2. The combined organic layers were dried with MgSO4, filtered, and concentrated. The residue was chromatographed on an analogix SF40-150 g column and eluted with 20% to 50% EtOAc/hexanes to obtain the title compound (5.2 g). [α]D=−91.1° (c=0.805, MeOH). MS (DCI+) m/z 324 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe combined organic layers were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on an analogix SF40-150 g column
  7. washeluted with 20% to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-77d50c94c5e94935b25244e8f4fa3b30
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

Loading…