Ethyl Acetate → HCID 131720399, compound

HRID 726796Notes

Reaction equation

HRID 726796 reaction equation
[NH:1]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@H:2]([C:18]([N:20]1[CH2:32][CH2:31][CH2:30][C@H:21]1[C:22]([NH:24][C@@H:25]([C:27]([NH2:29])=[O:28])[CH3:26])=[O:23])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1)=O.[H][H].CCOC(C)=O.[CH3:48][CH2:49][CH2:50]CCCC>CC(O)C.CC(C)=O.[Pd]>[NH:1]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[C@H:2]([C:18]([N:20]1[CH2:32][CH2:31][CH2:30][C@H:21]1[C:22]([NH:24][C@@H:25]([C:27]([NH2:29])=[O:28])[CH3:26])=[O:23])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][CH:49]([CH3:50])[CH3:48]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 100979753HCID 100979753, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131720399HCID 131720399, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

A solution of Boc-Lys(Cbz)-Pro-D-Ala-NH2 (80 gm) in 2-propanol (IPA, 800 mL) and acetone (108 mL) was hydrogenated over 4% Pd/C at 60 psi hydrogen. The catalyst was filtered off and rinsed with EtOAc, and the filtrate evaporated in vacuo to dryness. The residue was taken up in EtOAc (700 mL) and again evaporated in vacuo to dryness, and this procedure was repeated once. After dissolving the residue in EtOAc (250 mL) the solution was triturated with heptane (200 mL). The mixture was evaporated in vacuo to yield a solid which formed a suspension when treated with EtOAc (250 mL). The suspension was treated with heptane (100 mL), filtered and dried in vacuo to yield 64.2 gm Boc-Lys(iPr)-Pro-D-Ala-NH2. HPLC: 98.5 pa %, MS: (M+H)+ =456

Workup

  1. filtrationThe catalyst was filtered off
  2. washrinsed with EtOAc
  3. customthe filtrate evaporated in vacuo to dryness
  4. customagain evaporated in vacuo to dryness
  5. dissolutionAfter dissolving the residue in EtOAc (250 mL) the solution
  6. customwas triturated with heptane (200 mL)
  7. customThe mixture was evaporated in vacuo
  8. customto yield a solid which
  9. customformed a suspension when
  10. filtrationfiltered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-17618812766e479dbdec718685db074f
Source dataset
uspto-grants-1998_01
Patent number
US05710246

Reaction notes

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