1,2-Dichloroethane → Tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamate

HRID 1908275Notes

Reaction equation

HRID 1908275 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:10]([OH:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:22]1([NH2:25])[CH2:24][CH2:23]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>ClCCl>[CH:22]1([NH:25][C:11](=[O:13])[CH:10]([OH:14])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:24][CH2:23]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 34203793-tert-Butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid

Product 1

HCID 66645006Tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamateYield 114.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid (3 g, 10.16 mmol), cyclopropanamine (780 μL, 11.26 mmol) in dichloromethane (70 ml) at 5° C. EDC (2.4 g, 12.52 mmol), HOBt (1.9 g, 12.41 mmol) and Et3N (3 ml, 21.52 mmol) were added and the mixture stirred at room temperature for 48 h. After completion of reaction dichloromethane (100 ml) was added, the solution washed with water and brine, dried, filtered off with suction and concentrated to give 3.9 g of a brown oil which was purified further via chromatography on silica gel (eluent: CH2Cl2+5-30% (v/v) methanol). After evaporation of the combined product fractions 0.82 g of a pale oil were obtained; ESI-MS [M-Boc+H]±: 235.1.

Workup

  1. customat 5° C
  2. additionwas added
  3. washthe solution washed with water and brine
  4. customdried
  5. filtrationfiltered off with suction
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-908b1fc04e6349fcbf64d8ff0c4dcf4c
Source dataset
uspto-grants-2013_12
Patent number
US08598211B2

Reaction notes

Loading…