1,2-Dichloroethane → HCID 19705557, compound

HRID 727581Notes

Reaction equation

HRID 727581 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:14]1([C:28]([CH3:30])=[CH2:29])[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]1=[O:27])[C:11]([OH:13])=O)=[O:6].ClCl.CN(C=O)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1.Cl.[CH2:64]([O:71][NH2:72])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:14]1([C:28]([CH3:30])=[CH2:29])[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]1=[O:27])[C:11]([NH:72][O:71][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:13])=[O:6]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 79724-Methylmorpholine2×HCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 19705437HCID 19705437, compoundHCID 86751989HCID 86751989, compound

Product 1

HCID 19705557HCID 19705557, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A cold (0° C.) solution of α-[2-[(3,4-difluorobenzoyl)amino]ethyl]-2-oxo-1-(2-phenylethyl)-3-(propen-2-yl)-3-pyrrolidineacetic acid (427 mg, 0.908 mmol) in 2:1 CH2 Cl2 /DMF (6 mL) is treated with HOBT (147 mg, 1.09 mmol), EDC (209 mg, 1.09 mmol), and 4-methylmorpholine (120 μL, 1.09 mmol). The ice bath is removed, and after 1 hour, a second portion of 4-methylmorpholine (150 μL, 1.36 mmol) and O-benzylhydroxylamine HCl (217 mg, 1.36 mmol) are added. The solution is stirred overnight at room temperature under N2. The solution is diluted with EtOAc (25 mL) and washed with 1N HCl (10 mL), 1N NaOH (10 mL), H2O (2×10 mL), and brine (10 mL). The organic layer is dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 530 mg of a yellow solid. The solid is purified by silica gel chromatography (30 g SG; 50% EtOAc/hexane) to provide 373 mg (71%) of the title compound as a white, amorphous solid:

Workup

  1. customThe ice bath is removed
  2. washwashed with 1N HCl (10 mL), 1N NaOH (10 mL), H2O (2×10 mL), and brine (10 mL)
  3. dry with materialThe organic layer is dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-877f6dfa08224d67994da6b5aa52a19e
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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