Ammonium formate → HCID 54366979, compound

HRID 1781308Notes

Reaction equation

HRID 1781308 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][CH:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[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]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[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 86750877HCID 86750877, compound

Product 1

HCID 54366979HCID 54366979, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The procedure is similar to that described in Example 1, but starting with 2.58 g of benzyl (4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-benzyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenylacetate (isomer A) , 1.6 g of ammonium formate and 1.3 g of palladium on charcoal (10% Pd). 1.06 g of (4R) -3-{3-[2-(4-tert-butoxycarbonyl-2-benzyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenylacetic acid (isomer A), melting point 110° C., are thereby obtained; [α]D25 =-89.0°±1.6° (C %=0.51; methanol).

Sources & evidence

ORD record
ord-ffb54698da8d46458dc9823e743c6180
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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