3-Methoxyphenyl isocyanate → tert-butyl (2RS,5SR)-1-{2-[3-(3-methoxyphenyl)ureido]acetyl}-5-phenylprolinate

HRID 975939Notes

Reaction equation

HRID 975939 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH2:12][CH2:13][C:14]([N:16]1[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][CH2:25][CH:17]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:11])[NH:12][CH2:13][C:14]([N:16]2[CH:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:26][CH2:25][CH:17]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 878433-Methoxyphenyl isocyanateHCID 18928063HCID 18928063, compound

Product 1

HCID 131719900tert-butyl (2RS,5SR)-1-{2-[3-(3-methoxyphenyl)ureido]acetyl}-5-phenylprolinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

0.9 cm3 of 3-methoxyphenyl isocyanate is added to a solution of 2 g of tert-butyl (2RS,5SR)-1-(2-aminoacetyl)-5-phenylprolinate in 20 cm3 of anhydrous tetrahydrofuran. The reaction mixture is stirred for 20 hours at a temperature in the vicinity of 25° C. After evaporation of the solvent under reduced pressure at a temperature in the vicinity of 45° C., the crude product obtained is purified by chromatography on silica [eluent: dichloromethane/methanol (95/5 by volume)]. The fractions containing the expected product are combined, then concentrated to dryness under reduced pressure. After recrystallization in acetonitrile, 1.9 g of tert-butyl (2RS,5SR)-1-{2-[3-(3-methoxyphenyl)ureido]acetyl}-5-phenylprolinate melting at 174° C., are obtained.

Workup

  1. customAfter evaporation of the solvent under reduced pressure at a temperature in the vicinity of 45° C.
  2. customthe crude product obtained
  3. customis purified by chromatography on silica [eluent: dichloromethane/methanol (95/5 by volume)]
  4. additionThe fractions containing the expected product
  5. concentrationconcentrated to dryness under reduced pressure
  6. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-2a65aca1a87448bda0ffe18cfb4cce85
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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