1,2-Dichloroethane → HCID 86749455, compound

HRID 1721416Notes

Reaction equation

HRID 1721416 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][N:12]([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C@H:11]([C:21]([NH2:23])=[O:22])[CH2:10]1)=O)(C)(C)C.[C:24]1([CH:30]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:31][C:32](O)=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(Cl)CCl>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[NH2:8][C@H:9]1[CH2:13][N:12]([CH2:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[C@H:11]([C:21]([NH:23][C:32](=[O:33])[CH2:31][CH:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:22])[CH2:10]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 64798Diphenylpropionic acidHCID 757711-HydroxybenzotriazoleHCID 86749456HCID 86749456, compound

Product 1

HCID 86749455HCID 86749455, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 100 mg (0.31 mmol) of trans-4-(t-Butoxycarbonyl)aminocyclohexylmethyl L-proline amide, 70 mg (0.31 mmol) of 3,3 diphenylpropionic acid, 46 mg (0.34 mmol) of HOBT, and 34 mg (0.34 mmol) of triethylamine in 2 ml of anh. DMF under a nitrogen atmosphere was added 65 mg (0.34 mmol) of EDC. The resulting solution was stirred at room temp. for 18 h. The reaction was diluted with 2× its' volume of aq. 10% citric acid solution, and the mixture extracted 2× with EtOAc. The combined EtOAc extracts were washed with water and brine, and were dried over anh. MgSO4. Filtration and concentration gave crude product as a yellow oil. The product was purified via column chromatography over silica gel with 3:2 EtOAc/CHCL3 to give 109 mg (64%) of product as a clear glass.

Workup

  1. extractionthe mixture extracted 2× with EtOAc
  2. washThe combined EtOAc extracts were washed with water and brine
  3. dry with materialwere dried over anh. MgSO4
  4. filtrationFiltration and concentration
  5. customgave crude product as a yellow oil
  6. customThe product was purified via column chromatography over silica gel with 3:2 EtOAc/CHCL3

Sources & evidence

ORD record
ord-b6f389b6260a4f398556bab69637a5c9
Source dataset
uspto-grants-1996_04
Patent number
US05510369

Reaction notes

Loading…