1,2-Dichloroethane → HCID 22840071, compound

HRID 1721415Notes

Reaction equation

HRID 1721415 reaction equation
[C:1]([OH:11])(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=CC=CC=1.[CH:12]1[CH:13]=[CH:14][C:15]2N(O)N=N[C:16]=2[CH:17]=1.C[N:23]1CCO[CH2:25][CH2:24]1.[CH2:29](Cl)CCl.[Li+].[OH-]>C1COCC1.O.CC(N(C)C)=O>[CH2:24]([N:23]1[CH2:9][CH2:4][CH2:3][C@H:2]1[C:1]([OH:11])=[O:10])[CH2:25][CH2:29][C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:17]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 107Benzenepropanoic acidHCID 3939Lithium HydroxideHCID 79724-MethylmorpholineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 22840071HCID 22840071, compound

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Hydrocinnamic acid (1.63 g., 11 mmol) and L-proline-OMe HCl (2.19 g., 13.2 mmol) were dissolved in 110 ml. of dimethylacetamide (DMAc), followed by the addition of 2.19 g. (14.3 mmol) of HOBt and adjustment to pH 8 with N-methylmorpholine (NMM). Then EDC (3.16 g., 16.5 mmol) was added and the solution stirred for 20 hr., followed by concentration in vacuo and extractive workup with EtOAc to afford 2.97 g. of oily residue, which was purified by chromatography on silica gel to yield 2.68 g. of methyl ester. This intermediate was saponified in 100 ml. of 50:50 THF/H2O using 5.2 ml. of 2.17 N LiOH for 3 hr., to give, after acidification with dil. KHSO4, removal of the volatile solvents in vacuo, and extractive workup with EtOAc, the title compound as a colorless oil.

Workup

  1. concentration, followed by concentration in vacuo and extractive workup with EtOAc
  2. customto afford 2.97 g
  3. customof oily residue, which was purified by chromatography on silica gel
  4. customto yield 2.68 g
  5. custom, to give
  6. customafter acidification with dil. KHSO4, removal of the volatile solvents in vacuo, and extractive workup with EtOAc

Sources & evidence

ORD record
ord-3fca6b15ca1f4c4ba4a073b22d62c526
Source dataset
uspto-grants-1996_04
Patent number
US05510369

Reaction notes

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