tert-Butyl isocyanate → HCID 70976316, compound

HRID 535523Notes

Reaction equation

HRID 535523 reaction equation
[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]([NH:14][C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:4]=1.[N:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[C:26]=[O:27]>C(Cl)Cl>[C:28]([NH:25][C:26]([NH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]([NH:14][C:15](=[O:24])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:4]=1)=[O:27])([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 70976268HCID 70976268, compound

Product 1

HCID 70976316HCID 70976316, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product from Example 42 (13.8 mg, 0.040 mmol) and 2-isocyanato-2-methylpropane (5.2 μL, 0.044 mmol) in DCM (0.4 mL) was stirred at room temperature for 2 hours, concentrated, and chromatographed (5% MeOH/DCM) to give 12.1 mg of the title compound as a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 11.58-11.61 (bs, 1H), 8.32 (dd, J=7.8, 1.4 Hz, 1H), 8.14 (d, J=8.0 Hz, 1H), 7.98 (ddd, J=8.0, 7.2, 1.5 Hz, 1H), 7.90 (ddd, J=7.9, 7.2, 1.3 Hz, 1H), 7.41 (s, 4H), 6.19 (t, J=5.8 Hz, 1H), 5.81 (s, 1H), 4.50 (d, J=5.8 Hz, 2H), 3.68 (s, 2H), 1.22 (s, 9H); MS (ESI−) M/Z 440 (M−H)−, 486 (M+COOH)−.

Workup

  1. concentrationconcentrated
  2. customchromatographed (5% MeOH/DCM)

Sources & evidence

ORD record
ord-2893e5aabc2c4317a99d664292d8181f
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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