1,2-Dichloroethane → 4-(3-(Tert-butoxycarbonylamino)-1-(4-carbamoyl-3-fluorophenylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate

HRID 1944180Notes

Reaction equation

HRID 1944180 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:30])[CH:12]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=2)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][C:5]=1[F:31])(=[O:3])[NH2:2].C(Cl)CCl.[CH3:36][C:37]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:38]=1[C:39](O)=[O:40]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:36][C:37]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:38]=1[C:39]([O:29][CH2:28][C:25]1[CH:24]=[CH:23][C:22]([CH:12]([CH2:13][NH:14][C:15]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:21])[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:1](=[O:3])[NH2:2])=[C:5]([F:31])[CH:6]=2)=[O:30])=[CH:27][CH:26]=1)=[O:40]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 118972,4-Dimethylbenzoic acidHCID 59563726Tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamate

Product 1

HCID 595636994-(3-(Tert-butoxycarbonylamino)-1-(4-carbamoyl-3-fluorophenylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamate (E337-1) in pyridine was added was added EDC, DMAP, and 2,4-dimethylbenzoic acid, and the solution was stirred overnight at room temperature. The mixture was poured into NaHCO3(sat) and extracted with EtOAc. The organics were dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-5% MeOH/CH2Cl2 gradient) gave pure 4-(3-(tert-butoxycarbonylamino)-1-(4-carbamoyl-3-fluorophenylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate (E337-2).

Workup

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

Sources & evidence

ORD record
ord-2441bdb1a07f4f0199d038d208867088
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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