1,2-Dichloroethane → Tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propylcarbamate

HRID 1944178Notes

Reaction equation

HRID 1944178 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[CH:16][CH:15]=1)[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[NH2:36][C:37]1[CH:45]=[CH:44][C:40]([C:41]([NH2:43])=[O:42])=[C:39]([F:46])[CH:38]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:41]([C:40]1[CH:44]=[CH:45][C:37]([NH:36][C:11](=[O:13])[CH:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][Si:22]([CH:29]([CH3:30])[CH3:31])([CH:26]([CH3:27])[CH3:28])[CH:23]([CH3:24])[CH3:25])=[CH:16][CH:15]=2)[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:38][C:39]=1[F:46])(=[O:42])[NH2:43]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 230680054-Amino-2-fluoro-benzamideHCID 595637683-((tert-Butoxycarbonyl)amino)-2-(4-(((triisopropylsilyl)oxy)methyl)phenyl)propanoic acid

Product 1

HCID 59563790Tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propylcarbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 3-(tert-butoxycarbonylamino)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoic acid in pyridine was added EDC, DMAP, and 4-amino-2-fluorobenzamide (E336), and the solution was stirred overnight at room temperature. The mixture was poured into NaHCO3(sat) and extracted with EtOAc. The extracts were dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-6% MeOH/CH2Cl2 gradient) gave pure tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propylcarbamate (E337).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-be496fe95e214d6e8fafc78fcd8fb4fc
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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