Methanol → HCID 15788463, compound

HRID 976006Notes

Reaction equation

HRID 976006 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]1[C:19](=[O:43])[CH2:20][NH:21][C:22](=[O:42])[NH:23][C:24]1[CH:25]=[C:26]([CH:30]([CH3:41])[C:31]([O:33]CC2C=CC=CC=2)=[O:32])[CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]1[C:19](=[O:43])[CH2:20][NH:21][C:22](=[O:42])[NH:23][C:24]1[CH:25]=[C:26]([CH:30]([CH3:41])[C:31]([OH:33])=[O:32])[CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 887MethanolHCID 67713575HCID 67713575, compound

Product 1

HCID 15788463HCID 15788463, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The operation is carried out as in Example 84, but starting from 0.88 g of benzyl 2-{3-{3-[2-((2S,5R)-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenyl}propionate (B form) in solution in 50 cm3 of ethyl acetate and 0.22 g of 10% palladium on charcoal. After treatment, 0.5 g of 2-{3-{3-[2-((2S,5R)-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenyl}propionic acid (B form), melting at 120° C., [α]D20 =+49.8°±0.8° (c=0.53; methanol), is obtained.

Sources & evidence

ORD record
ord-2cac95b300774cfc907f95291b36e0a8
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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