Diisopropylcarbodiimide → 3-chloro-N'-{[(2R)-2-hydroxypropanoyl]oxy}benzenecarboximidamide

HRID 732090Notes

Reaction equation

HRID 732090 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[N:10][OH:11])[NH2:9])[CH:5]=[CH:6][CH:7]=1.[C:12](O)(=[O:16])[C@@H:13]([CH3:15])[OH:14].CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[N:10][O:11][C:12](=[O:16])[C@H:13]([OH:14])[CH3:15])[NH2:9])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 61503D-Lactic AcidHCID 757711-HydroxybenzotriazoleHCID 27948173-Chlorobenzamidoxime

Product 1

HCID 866020063-chloro-N'-{[(2R)-2-hydroxypropanoyl]oxy}benzenecarboximidamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3.82 g (22.4 mmol) of 3-chloro-N′-hydroxybenzenecarboximidamide and 2.00 g (22.2 mmol) of (R)-lactic acid were dissolved under Ar at 0° C. in DCM (50 mL) and DMF (15 mL). After 5 min 3.4 mL (33.2 mmol) DIC and 3.50 g (25.9 mmol) HOBt were added. After 15 min the mixture was warmed to r.t. and stirred for additional 3 h, followed by filtration and washing with DCM. The filtrate was evaporated in vacuo to near dryness, taken up in EA and washed with aq. NaHCO3, followed by water and finally 2 M aq. citric acid. The EA layer was filtered over a mixture of Na2SO4 and silica. Flash chromatography (Hep/EA=4/1 to 2/1 to 1/2) gave an oil which was triturated with Et2O to yield after drying 4 g (75%) of the title compound. 1H NMR: 7.69 (t, 1 H), 7.55-7.59 (m, 1 H), 7.44-7.49 (m, 1 H), 7.36 (t, 1 H), 5.10 (s, 2 H), 4.50 (q, 1 H), 1.54 (d, 3 H)

Workup

  1. filtrationfollowed by filtration
  2. washwashing with DCM
  3. customThe filtrate was evaporated in vacuo
  4. washwashed with aq. NaHCO3
  5. filtrationThe EA layer was filtered over a mixture of Na2SO4 and silica
  6. customFlash chromatography (Hep/EA=4/1 to 2/1 to 1/2) gave an oil which
  7. customwas triturated with Et2O
  8. customto yield
  9. dry with materialafter drying 4 g (75%) of the title compound

Sources & evidence

ORD record
ord-5ebaeb600b7b49889d7a3e192e63bfc5
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

Loading…