tert-Butanol → N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide

HRID 1969655Notes

Reaction equation

HRID 1969655 reaction equation
[CH:1]1([S:4]([NH:7][CH:8]2[CH2:12][CH:11](C(O)=O)[CH:10]([CH3:16])[CH2:9]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C1C=CC(P([N:31]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C[C:35]([OH:38])(C)C>>[N:31]([CH:11]1[CH:10]([CH3:16])[CH2:9][CH:8]([NH:7][S:4]([CH:1]2[CH2:2][CH2:3]2)(=[O:5])=[O:6])[CH2:12]1)=[C:35]=[O:38]

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 580099884-(Cyclopropanesulfonamido)-2-methylcyclopentanecarboxylic acid

Product 1

HCID 86660440N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamideYield 80%

Conditions

Temperature
70 °C

Procedure

To a solution of 4-(cyclopropanesulfonamido)-2-methylcyclopentanecarboxylic acid (4.10 g, 16.58 mmol, prepared from Example #24 Step I using Y, K, and Z) and DPPA (3.58 mL, 16.58 mmol) in t-BuOH (55 mL) was added TEA (5.0 mL, 36.5 mmol). The reaction was heated to about 70° C. for about 2 h then cooled to ambient temperature and concd under reduced pressure to afford a crude residue. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM to afford N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide (3.25 g, 80%) as a white solid: LC/MS (Table 1, Method n) Rt=0.49 min; MS m/z: 245 (M+H)+.

Workup

  1. temperaturethen cooled to ambient temperature
  2. customconcd under reduced pressure to afford a crude residue
  3. customThe crude material was purified by silica gel chromatography
  4. washeluting with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-94f027c0c04a4fe69ce37ff9c3912f0b
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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