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

HRID 24639Notes

Reaction equation

HRID 24639 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-a0f15e8df38f42b4a983f02beb6c2e83
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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