Ammonium formate → HCID 53926064, compound

HRID 1781315Notes

Reaction equation

HRID 1781315 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][C@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:9]1[C:25](=[O:48])[CH2:26][NH:27][C:28](=[O:47])[NH:29][C:30]1[CH:31]=[C:32]([CH2:36][C:37]([O:39]CC2C=CC=CC=2)=[O:38])[CH:33]=[CH:34][CH:35]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd]>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][C@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:9]1[C:25](=[O:48])[CH2:26][NH:27][C:28](=[O:47])[NH:29][C:30]1[CH:31]=[C:32]([CH2:36][C:37]([OH:39])=[O:38])[CH:33]=[CH:34][CH:35]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 53855200HCID 53855200, compound

Product 1

HCID 53926064HCID 53926064, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The procedure is similar to that described in Example 1, but starting with 1.36 g of benzyl (2R,4R)-3-[3-{2-[4-tert-butoxycarbonyl-2-(2-phenylphenyl)-3-thiazolidinyl]-2-oxoethyl}ureido]phenylacetate, 0.44 g of ammonium formate and 0.6 g of palladium on charcoal (10% Pd). 0.25 g of (2R,4R)-3-[3-{2-[4-tert-butoxycarbonyl-2-(2-phenylphenyl)-3-thiazolidinyl]-2-oxoethyl}ureido]phenylacetic acid, melting point 128° C., is thereby obtained; [α]D25 =-26.2°±0.9° (C %=0.56; MeOH).

Sources & evidence

ORD record
ord-b47779451583489f80b26bac401c4f5d
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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