Tetrahydrofuran → HCID 15819191, compound

HRID 2293789Notes

Reaction equation

HRID 2293789 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[C@@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@@H:8]([C:16]([O:18][CH3:19])=[O:17])[S:7][C@H:6]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:4].O1[CH2:31][CH2:30][CH2:29][CH2:28]1>CC1C=C(N=C=O)C=CC=1>[CH3:19][O:18][C:16]([C@H:8]1[S:7][C@@H:6]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:5]([C:3](=[O:4])[CH2:2][NH:1][C:3]([NH:5][C:9]2[CH:10]=[CH:31][CH:30]=[C:29]([CH3:28])[CH:8]=2)=[O:4])[C@H:9]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:17]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86751592HCID 86751592, compound

Product 1

HCID 15819191HCID 15819191, compound

Reagents, catalysts & solvents 1

HCID 69303m-Tolyl isocyanateSolvent

Procedure

The process is performed in a similar manner to that described in Example 1, but starting with a solution containing 0.7 g of tert-butyl (2S,4S,5S)-3-(2-aminoacetyl)-5-methoxycarbonyl-4-phenyl-2-thiazolidinecarboxylate in 20 ml of tetrahydrofuran and 250 μl of 3-methylphenyl isocyanate. The crude product is purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (20/80 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. 0.28 g of tert-butyl (2S,4S,5S)-5-methoxycarbonyl-3-{2-[3-(3-methylphenyl)ureido]acetyl}-4-phenyl-2-thiazolidinecarboxylate is thus obtained in the form of a white foam, Rf=0.39 [ethyl acetate/cyclohexane (50/50 in volume)]; 1H NMR (200 MHz, (CD3)2SO with addition of a few drops of CD3COOD, at a temperature of 297 K, δ in ppm): 1.48 (s, 9H: CH3 of the tert-butyl); 2.21 (s, 3H: ArCH3); 3.28 and 4.15 (broad d and d respectively, J=17.5 Hz, 1H each: COCH2N); 3.37 (s, 3H: COOCH3); 5.10 (d, J=7 Hz, 1H: H at C5 of the ring); 5.43 (s, 1H: H at C2 of the ring); 5.68 (d, J=7 Hz, 1H: H at C4 of the ring); 6.70 (broad d, J=7.5 Hz, 1H: aromatic H (H ortho to the CH3)); 7.06 (t, J=7.5 Hz, 1H: aromatic H (H meta to the CH3)); from 7.00 to 7.50 (mt, 5H: aromatic H); 7.72 (mt, 2H: H ortho to the phenyl).

Workup

  1. customThe crude product is purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (20/80 by volume)]
  2. additionThe fractions containing the expected product
  3. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-b8a504e99b5b4c189b809a3f68cdc8c7
Source dataset
uspto-grants-1997_11
Patent number
US05686622

Reaction notes

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