Isocyanate → 5-(R)-(4-bromobenzyl)-3-(5-amino-3-chlorophenyl)-5-methylimidazoline-2,4-dione

HRID 275827Notes

Reaction equation

HRID 275827 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C@@:7]2([CH3:25])[NH:11][C:10](=[O:12])[N:9]([C:13]3[CH:18]=[C:17]([NH:19]C(C)=O)[CH:16]=[C:15]([Cl:23])[CH:14]=3)[C:8]2=[O:24])=[CH:4][CH:3]=1.[N-]=C=O.COC(=O)[C@@](C)(CC1C=CC(Br)=CC=1)N.N(C1C=C(Cl)C=C(C=1)N)C(C)=O>Cl>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C@@:7]2([CH3:25])[NH:11][C:10](=[O:12])[N:9]([C:13]3[CH:18]=[C:17]([NH2:19])[CH:16]=[C:15]([Cl:23])[CH:14]=3)[C:8]2=[O:24])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 105034IsocyanateHCID 155463215-(R)-(4-bromobenzyl)-3-(5-acetamino-3-chlorophenyl)-5-methylimidazoline-2,4-dioneHCID 16079742(R)-alpha-methyl-4-bromophenylalanine methyl esterHCID 18542894HCID 18542894, compound

Product 1

HCID 155463225-(R)-(4-bromobenzyl)-3-(5-amino-3-chlorophenyl)-5-methylimidazoline-2,4-dione

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(R)-(4-bromobenzyl)-3-(5-acetamino-3-chlorophenyl)-5-methylimidazoline-2,4-dione (prepared by the process described in Example 1 from the isocyanate derivative of (R)-α-methyl-4-bromophenylalanine methyl ester and 5-acetamino-3-chloroaniline) was hydrolyzed by heating in 2N HCl to give 5-(R)-(4-bromobenzyl)-3-(5-amino-3-chlorophenyl)-5-methylimidazoline-2,4-dione. Sandmeyer reaction with NaNO2, CuCN and KCN provided the title compound as a resin.

Sources & evidence

ORD record
ord-c90f84d5985d47aaaab965f45582a923
Source dataset
uspto-grants-2002_03
Patent number
US06353013B1

Reaction notes

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