1,2-Dichloroethane → HCID 86678252, compound

HRID 537378Notes

Reaction equation

HRID 537378 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[C:10]([CH3:13])([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)Cl.[CH2:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)CCl>CN(C)C1C=CN=CC=1.C(OCC)C>[C:4]([O:3][C:1]([NH:8][C@H:9]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:14]([O:16][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:15])=[O:2])([CH3:6])([CH3:7])[CH3:5]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 6344DichloromethaneHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 86678252HCID 86678252, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

A 2-dram vial containing a small stirbar was charged with Boc-tert-leucine (10a) (10 mg, 0.04 mmol), CH2Cl2 (1 mL), 4-dimethylaminopyridine (2 mg, 0.02 mmol, 0.5 equiv), benzyl alcohol (20 μL, 0.2 mmol, 5 equiv), and EDC (20 mg, 0.1 mmol, 2.5 equiv). The solution was stirred at room temperature for 3 h, and then diluted with 10 mL of diethyl ether. The mixture was washed with water (2×10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue can be further purified by flash column chromatography on silica gel (7:1 hexanes/Et2O). Both the crude and purified samples were analyzed by chiral HPLC analysis: (AD-H, 1 mL/min, 5% IPA/hexanes, 210 nm): tR(major)=9.08 min, tR(minor)=15.80 min.

Workup

  1. additionA 2-dram vial containing a small stirbar
  2. washThe mixture was washed with water (2×10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue can be further purified by flash column chromatography on silica gel (7:1 hexanes/Et2O)
  6. customBoth the crude and purified samples
  7. custom=9.08 min
  8. customtR(minor)=15.80 min.

Sources & evidence

ORD record
ord-569d951208d540feb44928600cee86d3
Source dataset
uspto-grants-2014_10
Patent number
US08859812B2

Reaction notes

Loading…