1,2-Dichloroethane → HCID 21114343, compound

HRID 271959Notes

Reaction equation

HRID 271959 reaction equation
[C:1]([O:5][C:6]([N:8]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@@H:9]([C:25]([OH:27])=O)[CH2:10][CH2:11][C@@H:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[F:24])[CH:13]([CH2:15][OH:16])[NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:24][C:18]1[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:17]=1[C@H:12]1[CH:13]([CH2:15][OH:16])[NH:14][C:25](=[O:27])[C@H:9]([N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 68432014(5S)-N2,N2-bis(tert-Butoxycarbonyl)-5-(2,3-difluorophenyl)-6-(hydroxymethyl)-D-lysine

Product 1

HCID 21114343HCID 21114343, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (5S)-N2,N2-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-(hydroxymethyl)-D-lysine (180 mg, 0.37 mmol) in DCM (5 mL) were added EDC (106 mg, 0.55 mmol) and HOAT (50 mg, 0.37 mmol). After 30 min, NaHCO3 was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered and concentrated and the residue purified by silica gel chromatography (0%→10% MeOH/DCM) to give the title compound (100 mg). MS 471.1 (M+1).

Workup

  1. customthe layers separated
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue purified by silica gel chromatography (0%→10% MeOH/DCM)

Sources & evidence

ORD record
ord-d289a5375828427c9b3a264d2b9951ae
Source dataset
uspto-grants-2008_11
Patent number
US07452903B2

Reaction notes

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