Ammonium formate → HCID 10070574, compound

HRID 1066710Notes

Reaction equation

HRID 1066710 reaction equation
[NH:1]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:2]([C:19]([O:21]CC1C=CC=CC=1)=[O:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.C([O-])=O.[NH4+]>CO.C(O)(=O)C.[Pd]>[NH:1]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[C@H:2]([C:19]([OH:21])=[O:20])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 131722626HCID 131722626, compound

Product 1

HCID 10070574HCID 10070574, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

The title compound was prepared by reaction of crude BocTyr(PO3Et2)OBzl (1 mmol) and ammonium formate (4 mmol) with 10% Pd on charcoal for 20 min. at 50° C. in methanol/acetic acid mixture. After the filtration of the catalyst the solvent was concentrated in vacuo and the residue was dissolved in EtOAc and washed several times with a solution of satured NaCl. The organic phase was dried (Na2SO4) and concentrated, giving an oil 270 mg (70% yield), that was used without purification for the next step. FAB mass spectroscopy: m/z 409 [MNa]+. H1NMR (200 mhz, DMSO-d6) d (ppm)=7.3-7 (dd, 4H, aromatics), 4.1 (m, 4H, P—O—CH2—CH3), 3-2.7 (m, 2H, CH—CH2—F), 1.4-1.2 (m, 15H, CH3—CH2+tBu).

Workup

  1. filtrationAfter the filtration of the catalyst the solvent
  2. concentrationwas concentrated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed several times with a solution of satured NaCl
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce3d0dc52d4f419e8e3d70e7009faf9a
Source dataset
uspto-grants-2001_06
Patent number
US06245742B1

Reaction notes

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