Methyl chloroformate → N-(2,6-dichlorobenzoyl)-4-[2-(methoxycarbonylamino)phenyl]-L-phenylalanine methyl ester

HRID 1060411Notes

Reaction equation

HRID 1060411 reaction equation
OC(C(F)(F)F)=O.[CH3:8][O:9][C:10](=[O:37])[C@H:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH2:36])=[CH:26][CH:25]=1)[NH:12][C:13](=[O:22])[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21].CCN(C(C)C)C(C)C.Cl[C:48]([O:50][CH3:51])=[O:49]>C1COCC1>[CH3:8][O:9][C:10](=[O:37])[C@H:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][C:48]([O:50][CH3:51])=[O:49])=[CH:26][CH:25]=1)[NH:12][C:13](=[O:22])[C:14]1[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 131723775N-(2,6-dichlorobenzoyl)-4-(2-aminophenyl)-L-phenylalanine methyl ester TFA salt

Product 1

HCID 53637330N-(2,6-dichlorobenzoyl)-4-[2-(methoxycarbonylamino)phenyl]-L-phenylalanine methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2-aminophenyl)-L-phenylalanine methyl ester TFA salt (90 mg) was dissolved in THF (5 mL) and to this solution was added DIEA (160 μL) and ClCOOMe (20 μL). The mixture was stirred at room temperature for 12 h. After usual work-up as shown in Example 25, N-(2,6-dichlorobenzoyl)-4-[2-(methoxycarbonylamino)phenyl]-L-phenylalanine methyl ester was obtained.

Sources & evidence

ORD record
ord-4d5ec18b125741048c58ea54ace1511c
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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