m-Tolyl isocyanate → HCID 14996911, compound
Reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:6][C:7]([N:9]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:8])=[O:4].[CH3:30][C:31]1[CH:32]=[C:33]([N:37]=[C:38]=[O:39])[CH:34]=[CH:35][CH:36]=1>>[CH3:30][C:31]1[CH:32]=[C:33]([NH:37][C:38](=[O:39])[NH:1][CH2:2][C:3]([N:5]([CH2:6][C:7]([N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:8])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:4])[CH:34]=[CH:35][CH:36]=1Participants
Procedure
The procedure is analogous to that described in Example 1, but 1.4 g of tert-butyl N-{2-[(2-aminoacetyl)phenylamino]acetyl}-N-phenylglycinate and 0.45 g of 3-methylphenyl isocyanate are used as the starting material. The product obtained is purified by chromatography on 80 g of silica (0.04-0.063 mm) contained in a column 3 cm in diameter [eluent: methylene chloride/methanol (98-2 by volume)] using an excess pressure of 30 kPa of nitrogen and collecting 35 cm3 fractions. Fractions 19 to 21 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After churning the residue obtained with 25 cm3 of heptane, 0.4 g of tert-butyl N-{2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetyl}-N-phenylglycinate melting at 76°-80° C. is obtained.
Workup
- customThe product obtained
- customis purified by chromatography on 80 g of silica (0.04-0.063 mm)
- customcollecting 35 cm3 fractions
- concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
- customobtained with 25 cm3 of heptane
Sources & evidence
- ORD record
- ord-252ff8d542b54d08ad7e971aa219aa43
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05382590
Reaction notes
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