Dicyclohexylcarbodiimide → HCID 86750532, compound

HRID 975959Notes

Reaction equation

HRID 975959 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][C:21]1[CH:22]=[C:23]([NH:27][C:28](=[O:34])[NH:29][CH2:30][C:31](O)=[O:32])[CH:24]=[CH:25][CH:26]=1.C1(N=C=NC2CCCCC2)CCCCC1.[K+].[Br-]>CCCCCCC.CN(C=O)C>[CH3:20][C:21]1[CH:22]=[C:23]([NH:27][C:28](=[O:34])[NH:29][CH2:30][C:31]([N:9]2[C@H:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:12][S:11][C@@H:10]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[O:32])[CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 253877Potassium BromideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 22870470HCID 22870470, compound

Product 1

HCID 86750532HCID 86750532, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

The operation is carried out in a fashion similar to that described in Example 33, but starting from 3.5 g of tert-butyl-(2RS,4R)-2-(2-fluorophenyl)-4-thiazolidinecarboxylate, 2.3 g of 2-[3-(3-methylphenyl)ureido]acetic acid and 2.3 g of N,N'-dicyclohexylcarbodiimide. After vigorous stirring in heptane, 1.05 g of tert-butyl (2R,4R)-3-{2-[3-(3-methylphenyl)ureido]acetyl}-2-(2-fluorophenyl)-4-thiazolidinecarboxylate are thus obtained in the form of a white solid, melting at 107° C. ([α]D20 =+61.8°±1.5° (C=0.66%; DMF)) [proton NMR (200 MHz, DMSO D6, δ in ppm), 2 rotamers at room temperature, peak coalescence at 120° C., characteristic chemical shifts at 120° C.: 2.2 (bs, 3H, CH3); 6.7 (bd, 1H, N--C6H4 --C in position 4 or 6); 7.1 to 7.40 (m, 6H, aromatic); 7.9 (bm, 1H, C6H4F in position 3). Infrared spectrum (KBr), characteristics bands in cm-1 : 3370, 2975, 2925, 1735, 1645, 1615, 1590, 1560, 1490, 1460, 1370, 1150, 775, 760, 690].

Sources & evidence

ORD record
ord-09a6cdc8e942463189244bc36f1092df
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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