Methanol → 1-Carbamoyl-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethane

HRID 987129Notes

Reaction equation

HRID 987129 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:29][CH2:30][CH3:31])[C:26](O)=[O:27])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.[N:39]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.ClCCl.CO>CN(C=O)C>[C:26]([CH:25]([O:29][CH2:30][CH3:31])[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:10][CH:11]=2)=[CH:19][CH:20]=1)(=[O:27])[NH2:39]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 2724699PyBOPHCID 229884463-{4-[2-(4-tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid

Product 1

HCID 229884671-Carbamoyl-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethaneYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-{4-[2-(4-tert-Butoxycarbonylamino phenyl}ethoxy]phenyl]-2-ethoxypropanoic acid (1.18 g, 2.75 mmole) and benzotriazol-1-yl-oxytri-pyrrolidinophosphoniumhexafluorophosphate (1.43 g, 2.75 mmole) were dissolved in dry DMF (20 ml). Ammonia gas was bubbled through the mixture for 5 minutes. After stirring at room temperature for 16 hours it was checked using HPLC that all the starting material was consumed. Water was added and extracted three times with ethyl acetate dried with magnesium sulfate and evaporated. The residue was redissolved in dichloromethane and chromatography on silica using a gradient system of dichloromethane:methanol (0-5%) gave 1.04 g (85% yield) of the desired product.

Workup

  1. customAmmonia gas was bubbled through the mixture for 5 minutes
  2. customwas consumed
  3. additionWater was added
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue was redissolved in dichloromethane

Sources & evidence

ORD record
ord-2b7aefd4e38a42a0862be64f64aed055
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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