tert-Butyl (3-aminopropyl)carbamate → (3-{3-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ureido}-propyl)-carbamic acid tert-butyl ester

HRID 341172Notes

Reaction equation

HRID 341172 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH2:11])([CH3:4])([CH3:3])[CH3:2].[N:13]([C:16]1[CH:17]=[C:18]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)[CH:19]=[CH:20][CH:21]=1)=[C:14]=[O:15]>C1COCC1>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:14]([NH:13][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)[CH:17]=1)=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 441187472-(3-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 59320777(3-{3-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ureido}-propyl)-carbamic acid tert-butyl esterYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3-Amino-propyl)-carbamic acid tert-butyl ester (0.79 ml, 4.5 mmol) was added slowly to a stirred solution of 2-(3-isocyanato-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1 g, 4.1 mmol) in dry THF (8 ml) at RT under N2 After 16 hours the volatiles were removed in vacuo and the residue was partitioned between EtOAc/H2O. The organic layer was washed with brine (×1), then dried (Na2SO4), filtered and evaporated to give the title compound (1.6 g) as a colourless solid. 1H NMR (400 MHz, DMSO-d6): 8.52 (1H, s), 7.77 (1H, s), 7.47 (1H, dt), 7.25-7.17 (2H, m), 6.80 (1H, t), 6.08 (1H, t), 3.13-3.02 (2H, m), 3.02-2.89 (2H, m), 1.57-1.48 (2H, m), 1.39 (9H, s), 1.29 (12H, s).

Workup

  1. customwere removed in vacuo
  2. customthe residue was partitioned between EtOAc/H2O
  3. washThe organic layer was washed with brine (×1)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-117891b11ff7442d8ccf61a85f2264e2
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

Loading…