m-Tolyl isocyanate → HCID 9827815, compound

HRID 2293788Notes

Reaction equation

HRID 2293788 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[NH2:11][CH2:12][C:13]([N:15]1[C@@H:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:18]([C:26]([O:28][CH3:29])=[O:27])[S:17][C@H:16]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:14]>O1CCCC1>[CH3:29][O:28][C:26]([C@@H:18]1[S:17][C@@H:16]([C:30]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])[N:15]([C:13](=[O:14])[CH2:12][NH:11][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[O:10])[C@H:19]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:27]

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 15819190HCID 15819190, compound

Product 1

HCID 9827815HCID 9827815, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

50 μl of 3-methylphenyl isocyanate are added to a round-bottomed flask containing 0.14 g of tert-butyl (2S,4S,5R)-3-(2-aminoacetyl)-5-methoxycarbonyl-4-phenyl-2-thiazolidinecarboxylate dissolved in 10 ml of tetrahydrofuran. The reaction mixture is stirred for 12 hours at a temperature in the region of 25° C. and then concentrated to dryness under reduced pressure at 35° C. The crude product is purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (40/60 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. 0.13 g of tert-butyl (2S,4S,5R)-5-methoxycarbonyl-3-{2-[3-(3-methylphenyl)ureido]acetyl}-4-phenyl-2-thiazolidinecarboxylate is thus obtained in the form of a white foam, [α]D25 =-9.5°±0.8° (c=1.0; CH3OH), 1H NMR: (200 MHz, (CD3)2SO with addition of a few drops of CD3COOD, at a temperature of 373 K, δ in ppm): 1.51 (s, 9H: CH3 of the tert-butyl); 2.28 (s, 3H: ArCH3); 3.69 and 4.05 (broad d and d respectively, J=17 Hz, 1H each: COCH2N); 3.78 (s, 3H: COOCH3); 4.31 (d, J=3.5 Hz, 1H: at C5 of the ring); 5.75 (s, 1H: H at C2 of the ring); 5.86 (d, J=3.5 Hz, 1H: H at C4 of the ring); 6.76 (broad d, J=7.5 Hz, 1H: aromatic H (H ortho to the CH3)); 7.10 (t, J=7.5 Hz, 1H: aromatic H (H meta to the CH3) ); from 7.10 to 7.50 (mt, 5H: aromatic H); 7.73 (mt, 2H: H ortho to the phenyl).

Workup

  1. concentrationconcentrated to dryness under reduced pressure at 35° C
  2. customThe crude product is purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (40/60 by volume)]
  3. additionThe fractions containing the expected product
  4. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-3d6100c9fb074148af3ccee750241638
Source dataset
uspto-grants-1997_11
Patent number
US05686622

Reaction notes

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