tert-Butyl isocyanate → HCID 118061913, compound

HRID 920721Notes

Reaction equation

HRID 920721 reaction equation
[I:1][C:2]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[CH2:6][NH:7][CH2:8][CH2:9][N:4]2[N:3]=1.[N:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[C:17]=[O:18]>C1COCC1>[C:19]([NH:16][C:17]([N:7]1[CH2:8][CH2:9][N:4]2[N:3]=[C:2]([I:1])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[CH2:6]1)=[O:18])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 118062249HCID 118062249, compound

Product 1

HCID 118061913HCID 118061913, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Intermediate 104F (2.4 g, 7.47 mmol) in THF (20 mL) was added 2-isocyanato-2-methylpropane (0.741 g, 7.47 mmol) and the reaction mixture was stirred for 1.5 h. The volatiles were evaporated under reduced pressure. The crude was purified by silica gel chromatography (120 g REDISEP® column, eluting with 28% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate 104G (2.2 g, 70%). MS(ES): m/z=421 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 6.25 (s, 1H), 4.72 (s, 2H), 4.25 (q, J=6.8 Hz, 2H), 4.10 (t, J=5.24 Hz, 2H), 3.75 (m, 2H), 1.30 (t, J=7.2 Hz, 3H) 1.28 (s, 9H).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customThe crude was purified by silica gel chromatography (120 g REDISEP® column, eluting with 28% EtOAc in hexane)
  3. additionFractions containing the product
  4. customevaporated

Sources & evidence

ORD record
ord-639e2c6b77be48d3a75d8d0e2c21f48e
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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