4-Methylmorpholine → dimethyl N-(2-iodo-1-triphenylmethylimidazol-4-ylcarbonyl)-L-glutamate

HRID 1108278Notes

Reaction equation

HRID 1108278 reaction equation
[I:1][C:2]1[N:3]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=[C:5]([C:7](O)=[O:8])[N:6]=1.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.Cl.[NH2:48][C@H:49]([C:56]([O:58][CH3:59])=[O:57])[CH2:50][CH2:51][C:52]([O:54][CH3:55])=[O:53]>O1CCCC1>[I:1][C:2]1[N:3]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:4]=[C:5]([C:7]([NH:48][C@H:49]([C:56]([O:58][CH3:59])=[O:57])[CH2:50][CH2:51][C:52]([O:54][CH3:55])=[O:53])=[O:8])[N:6]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 12917568Dimethyl L-glutamate hydrochlorideHCID 187846222-Iodo-1-triphenylmethylimidazole-4-carboxylic acid

Product 1

HCID 54180859dimethyl N-(2-iodo-1-triphenylmethylimidazol-4-ylcarbonyl)-L-glutamateYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Iodo-1-triphenylmethylimidazole-4-carboxylic acid (1.443 g, 3.0 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (553 mg, 3.15 mmol), 4-methylmorpholine (0.614 mL, 6.6 mmol), dimethyl L-glutamate hydrochloride (698 mg, 3.3 mmol), and tetrahydrofuran (20 mL) were then allowed to react in the manner described in Example 15 to yield dimethyl N-(2-iodo-1-triphenylmethylimidazol-4-ylcarbonyl)--L-glutamate (1.44 g, 75%, mp 86-88° C.): 1H N (CDCl3) δ 7.47 (s, 1H), 7.44 (d, 1H, J=8.6 Hz), 7.32-7.26 (m, 9H), 7.21-7.05 (m, 6H), 4.72 (m, 1H), 3.71 (s, 3H), 3.62 (s, 3H), 2.41 (m, 2H), 2.27 (m, 1H), 1,99 (m, 1H). HRMS calcd for C30H28IN3O5 637.1074, found 637.1054. Anal. Calcd for C30H28IN3O5 : C, 56.52; H, 4.43; N, 6.59. Found: C, 56.36; H, 4.45, N, 6.57.

Workup

  1. customto react in the manner

Sources & evidence

ORD record
ord-3c7ee71810fe4f43b7058e3917c5cf8d
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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