Methanol → HCID 67764943, compound

HRID 1440085Notes

Reaction equation

HRID 1440085 reaction equation
[H][H].C(OCC)(=O)C.CCCCCC.[C:15]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:24]([NH:26][C@H:27]([C:35]([NH:37][C@H:38]([C:43]([OH:45])=[O:44])[CH2:39][CH:40]([CH3:42])[CH3:41])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])([OH:17])=[O:16].CO>C(O)C.[Pd].C(O)(=O)C.C1(C)C=CC=CC=1>[C:15]([C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[C:24]([NH:26][C@@H:27]([C:35]([NH:37][C@@H:38]([C:43]([OH:45])=[O:44])[CH2:39][CH:40]([CH3:41])[CH3:42])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])([OH:17])=[O:16]

Participants

9

Reactant 4

HCID 887MethanolHCID 21226206Ethyl acetate hexaneHCID 70431431HCID 70431431, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67764943HCID 67764943, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

An argon flushed solution of this phenylmethyl ester product (0.71 g., 1.2 mmole) in 95% ethanol (30 ml.) is treated with 10% palladium on carbon catalyst (70 mg.). The mixture is hydrogenated under a positive pressure of hydrogen, with thorough stirring, overnight at room temperature. After filtering the mixture through Celite, the filtrate is concentrated in vacuo to give 0.41 g. of a light brown solid. An analytical sample is prepared by recrystallization of 0.33 g. from ethyl acetate/hexane to yield 0.243 g. of white solid (trans)(R,R)-N-[N-[N-[(2-carboxycyclohexyl)carbonyl]-L-phenylalanyl]-L-leucine; m.p. 183.5°-185°. [α]D =39.8° (C =1.0, methanol). TLC (silica gel; toluene:acetic acid, 9:2) Rf =0.30.

Workup

  1. filtrationAfter filtering the mixture through Celite
  2. concentrationthe filtrate is concentrated in vacuo
  3. customto give 0.41 g
  4. customAn analytical sample is prepared by recrystallization of 0.33 g

Sources & evidence

ORD record
ord-eb9971657df84425b6886cda6b362854
Source dataset
uspto-grants-1996_03
Patent number
US05496805

Reaction notes

Loading…