Potassium Carbonate → (S)-3-(tert-butoxycarbonylamino)-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoic acid

HRID 1618332Notes

Reaction equation

HRID 1618332 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]([NH:15][C:16](=[O:47])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[N:29]=[C:28]([NH:30][C:31]3([C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:33][CH2:32]3)[N:27]=[C:26]([O:41][CH2:42][C:43]([F:46])([F:45])[F:44])[N:25]=2)=[CH:19][CH:18]=1)[C:11]([O:13]C)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]([NH:15][C:16](=[O:47])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[N:29]=[C:28]([NH:30][C:31]3([C:34]4[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=4)[CH2:32][CH2:33]3)[N:27]=[C:26]([O:41][CH2:42][C:43]([F:46])([F:45])[F:44])[N:25]=2)=[CH:19][CH:18]=1)[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3].[NH2:8][CH2:9][C@H:10]([NH:15][C:16](=[O:47])[C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:24]2[N:29]=[C:28]([NH:30][C:31]3([C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:32][CH2:33]3)[N:27]=[C:26]([O:41][CH2:42][C:43]([F:46])([F:45])[F:44])[N:25]=2)=[CH:21][CH:22]=1)[C:11]([OH:13])=[O:12]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 68182808(S)-methyl 3-(tert-butoxycarbonylamino)-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoate

Product 2

HCID 66765701(S)-3-(tert-butoxycarbonylamino)-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoic acidHCID 68183011(S)-3-amino-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of (S)-methyl 3-(tert-butoxycarbonylamino)-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoate (25 mg) and K2CO3 (25.4 mg) in acetone and water (1:1, 4 mL) was stirred at room temperature for 16 hours. The mixture was acidified to pH1. Solvents were removed under vacuum and the residue was purified by preparative HPLC to give (S)-3-(tert-butoxycarbonylamino)-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoic acid (15.6 mg) and (S)-3-amino-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoic acid (3.9 mg).

Workup

  1. customSolvents were removed under vacuum
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-dc2fbd331f2c47388937d4561b60a1d4
Source dataset
uspto-grants-2014_07
Patent number
US08765944B2

Reaction notes

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