Acetic Acid → HCID 131718330, compound

HRID 1974906Notes

Reaction equation

HRID 1974906 reaction equation
[NH:1]([C:32]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:33])[C@H:2]([C:7]([NH:9][C@@H:10]([C:22]([O:24]CC1C=CC=CC=1)=[O:23])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH3:21])[CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(O)(=O)C.CN(C=O)C.[H][H]>CO.[Pd]>[NH:1]([C:32]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:33])[C@H:2]([C:7]([NH:9][C@@H:10]([C:22]([OH:24])=[O:23])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH3:21])[CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 131718331HCID 131718331, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131718330HCID 131718330, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-phenylacetyl-L-Leu-D-Trp(CH3)-OBzl (5.9 g) in a mixture of methanol (60 ml), acetic acid (60 ml) and DMF (100 ml) was added 10% palladium on activated carbon (0.6 g). The mixture was stirred for 5 hours at 3 atmospheric pressure of hydrogen at room temperature. The solution was filtered and the filtrate was concentrated in vacuo. The residue was triturated with ether-ethyl acetate to give N-phenylacetyl-L-Leu-D-Trp(CH3)-OH (4.69 g).

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was triturated with ether-ethyl acetate

Sources & evidence

ORD record
ord-cd9604b6d28745fe8d1577863f3deb93
Source dataset
uspto-grants-1994_02
Patent number
US05284828

Reaction notes

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