1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 54318630, compound

HRID 975988Notes

Reaction equation

HRID 975988 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[C@H:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][S:7][C@@H:6]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:4].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][C:25]=1[C:33]([F:36])([F:35])[F:34]>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:32])[NH:1][CH2:2][C:3]([N:5]2[C@H:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][S:7][C@@H:6]2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:4])=[CH:26][C:25]=1[C:33]([F:34])([F:35])[F:36]

Participants

3

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 53866151HCID 53866151, compound

Product 1

HCID 54318630HCID 54318630, compoundYield 20.7%

Procedure

The operation is carried out in a fashion similar to that described in Example 34, but starting from 2.0 g of tert-butyl (2R,4R) 3-(2-aminoacetyl)-2-phenyl-4-thiazolidinecarboxylate and 1.6 g of 4-chloro-3-trifluoromethylphenyl isocyanate. The crude product obtained is purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (30/70 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. After vigorous stirring in 20 cm3 of hexane, 0.7 g of tert-butyl (2R,4R)-3-{2-[3-(4-chloro-3-tri-fluoromethylphenyl)ureido]acetyl}-2-phenyl-4-thiazolidinecarboxylate is thus obtained in the form of an amorphous powder, ([α]D20 =+58.2°±1.3° (C=0.49%; CH3OH), [proton NMR (250 MHz, DMSO D6, δ in ppm, J in Hz), 2 rotamers at room temperature, peak coalescence at 130° C., characteristic chemical shifts at 130° C.: 1.53 (s, 9H, --C(CH3)3); 3.29 and 3.47 (2dd, J=12.5 and 6.5, 2H, S--CH2 --); 3.73 (broad, 1H, of N--COCH2 --N); 4.10 (dd, J=17.5 and 4, 1H, the other H of N--COCH2 --N); 5.0 (broad, 1H, N--CH--COO); 6.33 (broad, 1H, --NHCO--); 6.4 (s, 1H, S--CH--N); 7.2 to 7.8 (m, 7H, aromatic); 7.97 (bs, 1H, in position 2 on CO--NH--Ph); 8.98 (broad, 1H, --CO--NH--Ph), [infrared spectrum (KBr), characteristic bands in cm-1 : 3375, 2980, 2930, 2875, 1740, 1640, 1595, 1550, 1485, 1455, 1370, 1325, 1175, 1150, 895, 730, 695].

Workup

  1. customThe crude product obtained
  2. customis purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (30/70 by volume)]
  3. additionThe fractions containing the expected product
  4. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-b8bd69157e3f4599bbc7abc11b4ebab7
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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