Ammonium formate → HCID 22872994, compound

HRID 1781311Notes

Reaction equation

HRID 1781311 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][CH:10]([CH:13]2[CH2:18][CH:17]3[CH2:19][CH:14]2[CH:15]=[CH:16]3)[N:9]1[C:20](=[O:43])[CH2:21][NH:22][C:23](=[O:42])[NH:24][C:25]1[CH:26]=[C:27]([CH2:31][C:32]([O:34]CC2C=CC=CC=2)=[O:33])[CH:28]=[CH:29][CH:30]=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][CH:10]([CH:13]2[CH2:18][CH:17]3[CH2:19][CH:14]2[CH2:15][CH2:16]3)[N:9]1[C:20](=[O:43])[CH2:21][NH:22][C:23](=[O:42])[NH:24][C:25]1[CH:26]=[C:27]([CH2:31][C:32]([OH:34])=[O:33])[CH:28]=[CH:29][CH:30]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 57104314HCID 57104314, compound

Product 1

HCID 22872994HCID 22872994, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The procedure is as in Example 1, but starting with 0.2 g of benzyl (4R)-3-[3-{2-[4-tert-butoxycarbonyl-2-[(2RS)-5-norbornen-2-yl]-3-thiazolidinyl]-2-oxoethyl}ureido]phenylacetate (mixture of isomers C and D), 0.13 g of Ammonium formate and 0.2 g of palladium on charcoal (10% Pd). 0.07 g of (4R)-3-[3-{2-[4-tert-butoxycarbonyl-2- ((2RS) -2-norbornyl)-3-thiazolidinyl]-2-oxoethyl}ureido]phenylacetic acid (mixture of isomers C and D) is thereby obtained in the form of a white product, melting point 115° C.

Sources & evidence

ORD record
ord-e052a83f32a340ebb3ba8deb4770dd4e
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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