1,2-Dichloroethane → HCID 59868529, compound

HRID 476295Notes

Reaction equation

HRID 476295 reaction equation
CCN(C(C)C)C(C)C.C(Cl)CCl.[C:14]([O:18][C:19]([NH:21][C@H:22]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:23][C:24](O)=[O:25])=[O:20])([CH3:17])([CH3:16])[CH3:15].C1C=CC2[N:42]([OH:43])N=NC=2C=1.Cl.NO.P(=O)(O)(O)O>CN(C=O)C.CCOC(C)=O.C1COCC1>[C:14]([O:18][C:19](=[O:20])[NH:21][C@H:22]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:23][C:24](=[O:25])[NH:42][OH:43])([CH3:17])([CH3:16])[CH3:15]

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 1004Phosphoric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 7021561(3R)-3-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid

Product 1

HCID 59868529HCID 59868529, compoundYield 6.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIPEA (32.7 mL, 188 mmol) and EDC (15.4 g, 80.5 mmol) were added to a solution of (R)-3-t-butoxycarbonylamino-4-phenylbutyric acid (15.0 g, 53.7 mmol), HOBt (7.3 g, 53.7 mmol), and hydroxylamine hydrochloride (7.5 g, 107 mmol) in DMF (150 mL). The mixture was stirred at room temperature for 1 day and then concentrated in vacuo to yield a pale yellow oil. The oil was distributed between 5% THF in EtOAc and IM phosphoric acid. The organic layer was collected and washed with 1M NaOH. The alkaline aqueous layer was then acidified using 1M phosphoric acid and extracted with EtOAc. The organic layer was evaporated and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to afford the title compound as a white solid (1.0 g, 3.4 mmol). MS m/z: [M+H+] calcd for C15H22N2O4, 295.16. found 295.2.

Workup

  1. concentrationconcentrated in vacuo
  2. customto yield a pale yellow oil
  3. customThe organic layer was collected
  4. washwashed with 1M NaOH
  5. extractionextracted with EtOAc
  6. customThe organic layer was evaporated
  7. customthe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ff85baf9394341c2b8c490e3f2381d69
Source dataset
uspto-grants-2014_01
Patent number
US08637676B2

Reaction notes

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