tert-butyl (2S,5R)-1-{2-[3-(3-(benzyloxycarbonyl)phenyl)ureido]acetyl}-5-isobutylpyrrolidine-2-carboxylate → Benzoic Acid

HRID 55107Notes

Reaction equation

HRID 55107 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13](NC(=O)NCC(N2[C@@H](CC(C)C)CC[C@H]2C(OC(C)(C)C)=O)=O)[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:9]([OH:10])(=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 57182634tert-butyl (2S,5R)-1-{2-[3-(3-(benzyloxycarbonyl)phenyl)ureido]acetyl}-5-isobutylpyrrolidine-2-carboxylate

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A The reaction is carried out in a way similar to that described in Example 1 A, but starting from 1.65 g of tert-butyl (2S,5R)-1-{2-[3-(3-(benzyloxycarbonyl)phenyl)ureido]acetyl}-5-isobutylpyrrolidine-2-carboxylate and 0.25 g of 10% palladium-on-charcoal in 50 cm3 of ethanol. After treatment, there is obtained 0.57 g of (2S,5R)-3-3-2-(2-tert-butoxycarbonyl-5-isobutyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid, the optical rotation of which is [α]D20 =-36.8° (c=1.0; methanol).

Sources & evidence

ORD record
ord-a442e4a8424d4524bcf2a9778c46fb1d
Source dataset
uspto-grants-1997_04
Patent number
US05624939

Reaction notes

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