Pyridoxal 5'-phosphate monohydrate → 5-{2-Chloro-5-[(tert-butylcarbonylamino)-methyl]-benzoylamino}-2,3-difluoro-benzoic acid

HRID 1846114Notes

Reaction equation

HRID 1846114 reaction equation
C(O[C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:19])=[C:14]([CH:18]=1)[C:15]([OH:17])=O)=[O:7])(C)(C)C.Cl[C:21](N(C)C)=[C:22]([CH3:24])[CH3:23].[NH2:28][C:29]1[CH:30]=[C:31]([F:39])[C:32]([F:38])=[C:33]([CH:37]=1)[C:34]([OH:36])=[O:35].CC1C(O)=C(C=O)C(COP(O)(O)=O)=CN=1.O>C1COCC1>[Cl:19][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6]([C:22]([CH3:21])([CH3:23])[CH3:24])=[O:7])=[CH:18][C:14]=1[C:15]([NH:28][C:29]1[CH:30]=[C:31]([F:39])[C:32]([F:38])=[C:33]([CH:37]=1)[C:34]([OH:36])=[O:35])=[O:17]

Participants

6

Reactant 4

HCID 38882Pyridoxal 5'-phosphate monohydrateHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 404270375-Amino-2,3-difluorobenzoic acidHCID 584833575-(((tert-Butoxycarbonyl)amino)methyl)-2-chlorobenzoic acid

Product 1

HCID 671164295-{2-Chloro-5-[(tert-butylcarbonylamino)-methyl]-benzoylamino}-2,3-difluoro-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to example 8 with 5-(tert-butoxycarbonylamino)methyl-2-chloro benzoic acid (0.2 g; 0.75 mmol); 1-chloro-N,N,2-trimethylpropenylamine (0.124 mL; 0.9 mmol); 5-amino-2,3-difluorobenzoic acid (0.13 g; 0.75 mmol) and TEA (0.261 mL; 0.88 mmol) in 20 mL THF. Yield: 290 mg (91%); MS: [m+H]+ 425; HPLC: Rt=1.29 min (Method MC-1)

Sources & evidence

ORD record
ord-d8bbdbf1a7ad4acf99e30867af85b6fe
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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