Diisopropylethylamine → Diethylbenzyl({[(1R)-1-phenylethyl]carbamoyl}amino)propanedioate

HRID 1526510Notes

Reaction equation

HRID 1526510 reaction equation
F[C:2](F)(F)[C:3](O)=O.C([N:10]([C:13]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:17]([OH:19])=[O:18])[C:14]([OH:16])=[O:15])CC)C.[CH:27](N(C(C)C)CC)(C)[CH3:28].[C:36]1([C@H:42]([N:44]=[C:45]=[O:46])[CH3:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O>[CH2:27]([O:16][C:14](=[O:15])[C:13]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([NH:10][C:45](=[O:46])[NH:44][C@@H:42]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:43])[C:17]([O:19][CH2:2][CH3:3])=[O:18])[CH3:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7018262(R)-(+)-1-Phenylethyl isocyanateHCID 89500110Diethylamino(benzyl)propanedioate trifluoroacetate

Product 1

HCID 89508911Diethylbenzyl({[(1R)-1-phenylethyl]carbamoyl}amino)propanedioate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the product from Step B (7.79 g, 20.54 mmol) in N,N-dimethylormamide (100 mL) was added diisopropylethylamine (10.76 mL, 61.6 mmol) at 0° C. the mixture was stirred for 5 min then (R)-(+)-1-phenylethyl isocyanate (3.76 mL, 26.7 mmol) was added dropwise. The mixture was warmed to ambient temperature over 30 min and stirred for 16 h. Water (150 mL) was added and a white solid crashed out, the mixture was filtered and the solid washed with water. The solid was diluted in ethyl acetate (250 mL) and half saturated aqueous sodium hydrogen carbonate (200 mL) was added and the mixture was extracted with ethyl acetate (4×50 mL). The combined organic fractions were washed with brine (saturated, 1×100 mL), dried with anhydrous sodium sulfate, filtered and the solvent removed in vacuo to afford the title compound as a colorless amorphous solid. LC/MS 413.1 (M+1).

Workup

  1. stirringstirred for 16 h
  2. filtrationthe mixture was filtered
  3. washthe solid washed with water
  4. additionThe solid was diluted in ethyl acetate (250 mL)
  5. additionhalf saturated aqueous sodium hydrogen carbonate (200 mL) was added
  6. extractionthe mixture was extracted with ethyl acetate (4×50 mL)
  7. washThe combined organic fractions were washed with brine (saturated, 1×100 mL)
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2418e1162e814a87ac0cbd840493a019
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

Loading…