Benzylamine → HCID 68540058, compound

HRID 1994310Notes

Reaction equation

HRID 1994310 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][CH:8]2[CH2:12]OS(=O)(=O)[N:9]2[CH:15]([CH:23]([CH3:25])[CH3:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:5][CH:4]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(#N)C>[CH2:34]([NH:41][CH2:12][CH:8]([NH:9][CH:15]([CH:23]([CH3:25])[CH3:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][C:6]1[CH:26]=[CH:27][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 10796Cesium carbonateHCID 86619842HCID 86619842, compound

Product 1

HCID 68540058HCID 68540058, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

t-Butyl 2-(4-(4-methoxybenzyl)-2,2-dioxo-(1,2,3) oxathiazolidin-3-yl)-3-methylbutyrate (1.0 g; 2.5 mmol) was dissolved in acetonitrile (15 ml). Cs2CO3 (1.63 g; 5 mmol) and benzylamine (0.5 ml; 4.5 mmol) were added, The reaction mixture was stirred at 55° C. for 4 h. It was then allowed to reach RT, and the reaction mixture was filtered through a clarifying layer. The residue was washed with acetonitrile. The filtrate was concentrated and taken up in CH2Cl2 (10 ml). Aqueous H2SO4 (20%; 5 ml) was added, and the mixture was stirred at RT for 1.5 h. The phases were then separated, the aqueous phase was extracted with CH2Cl2 (2×), and the combined organic phases were dried over Na2SO4 and concentrated in a rotary evaporator. The crude product was stirred with CH2Cl2/CH3CN/Et2O and concentrated. t-Butyl 2-(2-benzylamino-1-(4-methoxybenzyl)ethylamino)-3-methylbutyrate (1.15 g; 2.5 mmol) was obtained as a yellowish foam. MS: 427.20 (M+H); Rt: 1.42 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

  1. customto reach RT
  2. filtrationthe reaction mixture was filtered through a clarifying layer
  3. washThe residue was washed with acetonitrile
  4. concentrationThe filtrate was concentrated
  5. additionAqueous H2SO4 (20%; 5 ml) was added
  6. stirringthe mixture was stirred at RT for 1.5 h
  7. customThe phases were then separated
  8. extractionthe aqueous phase was extracted with CH2Cl2 (2×)
  9. dry with materialthe combined organic phases were dried over Na2SO4
  10. concentrationconcentrated in a rotary evaporator
  11. stirringThe crude product was stirred with CH2Cl2/CH3CN/Et2O
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-8d0140607cc847dda19925547ee64af2
Source dataset
uspto-grants-2010_01
Patent number
US07652143B2

Reaction notes

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