m-Tolyl isocyanate → HCID 54190686, compound

HRID 1781317Notes

Reaction equation

HRID 1781317 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][C:18]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:4].[CH3:29][C:30]1[CH:31]=[C:32]([N:36]=[C:37]=[O:38])[CH:33]=[CH:34][CH:35]=1>>[CH3:29][C:30]1[CH:31]=[C:32]([NH:36][C:37](=[O:38])[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:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:4])[CH:33]=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 54550236HCID 54550236, compound

Product 1

HCID 54190686HCID 54190686, compoundYield 12.5%

Procedure

The procedure is similar to that described in Example 1A, but starting with 1.32 g of tert-butyl (2R,4R)-3-(2-aminoacetyl)-2-(2-phenylphenyl)-4-thiazolidinecarboxylate and 0.47 g of 3-methylphenyl isocyanate. The crude product is purified by chromatography on silica [eluent: methylene chloride/ethyl acetate (90:10 by volume)]. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure at 40° C. After vigorous stirring in pentane, 0.22 g of tert-butyl (2R,4R)-3-{2-[3-(3-methylphenyl)-ureido]acetyl}-2-(2-phenylphenyl)-4-thiazolidinecarboxylate is thereby obtained in the form of an amorphous product; [α]D25 =-9.8±0.9° (C %=0.49; CHCl3).

Workup

  1. customThe crude product is purified by chromatography on silica [eluent: methylene chloride/ethyl acetate (90:10 by volume)]
  2. additionThe fractions containing the expected product
  3. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-e580b3e86a874597a7a65767dd4dd35e
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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