Acetyl chloride → HCID 70587793, compound

HRID 462212Notes

Reaction equation

HRID 462212 reaction equation
C([Cl:4])(=O)C.[CH3:5][O:6][C:7](=[O:39])[C@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32](=[O:34])[CH3:33])=[C:27]([O:35][C:36](=[O:38])[CH3:37])[CH:26]=1)[NH:9][C:10](=[O:23])[CH2:11][NH:12]C(OCC1C=CC=CC=1)=O>CO.C(O)(=O)C.Cl.CCOCC.[Pd]>[ClH:4].[CH3:5][O:6][C:7](=[O:39])[C@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32](=[O:34])[CH3:33])=[C:27]([O:35][C:36](=[O:38])[CH3:37])[CH:26]=1)[NH:9][C:10](=[O:23])[CH2:11][NH2:12]

Participants

8

Reactant 2

HCID 6367Acetyl chlorideHCID 70634138HCID 70634138, compound

Product 1

HCID 70587793HCID 70587793, compoundYield 24%

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Next, 3.00 g (6.17 millimole) of the above isolated ester was dissolved in methanol (100 ml) and glacial acetic acid (5 ml). The solution was then shaken in a Parr apparatus for 16 hours over 10% Pd/C (0.4 g) under a hydrogen atmosphere (35 lbs). The solution was then filtered and concentrated in vacuo at room temperature. The residue obtained was dissolved in 10 ml of glacial acetic acid, saturated with hydrogen chloride and treated with 10 ml of acetyl chloride. The solution was stirred at room temperature overnight in a tightly sealed reaction flask and then diluted to 125 ml with ether to give a light brown gum. The ether was decanted and the residue was suspended in anhydrous ether (100 ml). The suspended solid was dispersed with a spatula and allowed to stir unit it became homogeneous. It was then filtered and the residue was dried in a vacuum oven at 60° C to yield 0.58 g (mp 80°-100° C, 24% yield) of glycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester hydrochloride from carbobenzyloxyglycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester. The nmr spectrum was consistent with the proposed structure of the compound obtained and upon analysis of the compound, the following data was obtained. Analysis Calculated for: C16H21O7N2Cl: C, 49.42; H, 5.44; and N, 7.21. Found: C, 49.65; H, 5.50; and N, 7.47.

Workup

  1. filtrationThe solution was then filtered
  2. concentrationconcentrated in vacuo at room temperature
  3. customThe residue obtained
  4. customto give a light brown gum
  5. customThe ether was decanted
  6. additionThe suspended solid was dispersed with a spatula
  7. stirringto stir unit it
  8. filtrationIt was then filtered
  9. customthe residue was dried in a vacuum oven at 60° C

Sources & evidence

ORD record
ord-fefc7e439e9746c39cef5d2b60ae2ca0
Source dataset
uspto-grants-1977_12
Patent number
US04065566

Reaction notes

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