m-Tolyl isocyanate → HCID 57286235, compound

HRID 1781313Notes

Reaction equation

HRID 1781313 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][CH:6]1[CH2:17][CH2:18][CH2:19][CH3:20])=[O:4].[CH3:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1>>[CH3:21][C:22]1[CH:23]=[C:24]([NH:28][C:29](=[O:30])[NH:1][CH2:2][C:3]([N:5]2[C@H:9]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:8][S:7][CH:6]2[CH2:17][CH2:18][CH2:19][CH3:20])=[O:4])[CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 53727905HCID 53727905, compound

Product 1

HCID 57286235HCID 57286235, compoundYield 46.3%

Procedure

The procedure is similar to that described in Example 1A, but starting with 1.2 g of tert-butyl (4R)-3-(2-aminoacetyl)-2-butyl-4-thiazolidinecarboxylate (isomer A) and 0.53 g of 3-methylphenyl isocyanate. The crude product is purified by chromatography on silica [eluent: diisopropyl ether/ethyl acetate (95:5 by volume)]. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure at 40° C. 0.8 g of tert-butyl (4R)-3-{2-[3-(3-methylphenyl)-ureido]acetyl}-2-butyl-4-thiazolidinecarboxylate (isomer A) is thereby obtained in the form of an amorphous product; [α]D25 =-39°±1° (C %=0.53; DMF).

Workup

  1. customThe crude product is purified by chromatography on silica [eluent: diisopropyl ether/ethyl acetate (95:5 by volume)]
  2. additionThe fractions containing the expected product
  3. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-4bc9a35c6a6d473b92f6f84258e723b3
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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