Ammonium formate → HCID 53961903, compound

HRID 1781314Notes

Reaction equation

HRID 1781314 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][CH:10]([CH2:13][CH2:14][CH2:15][CH3:16])[N:9]1[C:17](=[O:39])[CH2:18][NH:19][C:20](=[O:38])[NH:21][C:22]1[CH:23]=[C:24]([CH:35]=[CH:36][CH:37]=1)[C:25]([O:27]CC1C=CC=CC=1)=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CN(C=O)C>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][CH:10]([CH2:13][CH2:14][CH2:15][CH3:16])[N:9]1[C:17](=[O:39])[CH2:18][NH:19][C:20](=[O:38])[NH:21][C:22]1[CH:23]=[C:24]([CH:35]=[CH:36][CH:37]=1)[C:25]([OH:27])=[O:26])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86750879HCID 86750879, compound

Product 1

HCID 53961903HCID 53961903, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The procedure is similar to that described in Example 1, but starting with 1.18 g of benzyl (4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-butyl-3-thiazolidinyl)-2-oxoethyl]ureido}benzoate (isomer A), 0.8 g of ammonium formate and 1.2 g of palladium on charcoal (10% Pd). 0.25 g of (4R) -3-{3- [2- (4-tert-butoxycarbonyl-2-butyl-3-thiazolidinyl)-2-oxoethyl]ureido}benzoic acid (isomer A) is thereby obtained in the form of an amorphous products [α]D25 =-35.4°±1.0° (C %=0.52; DMF).

Sources & evidence

ORD record
ord-e00d18b187a74148a66e17d1bf97c616
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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