tert-Butanol → HCID 131734380, compound

HRID 1507697Notes

Reaction equation

HRID 1507697 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].CCN(C(C)C)C(C)C.[CH2:22]([O:29][C:30]1[C:34]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:33][N:32]([C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)[C:31]=1[C:51]([N:53]([CH3:55])[CH3:54])=[O:52])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:36]([O:35][C:34]1[C:30]([O:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:31]([C:51](=[O:52])[N:53]([CH3:55])[CH3:54])[N:32]([C:43]2[CH:44]=[CH:45][C:46]([O:49][CH3:50])=[CH:47][CH:48]=2)[C:33]=1[S:2]([NH:5][C:6](=[O:7])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:4])=[O:3])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanateHCID 81531DiisopropylethylamineHCID 89610465HCID 89610465, compound

Product 1

HCID 131734380HCID 131734380, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

To a solution of chlorosulfonyl isocyanate (70.9 μL, 0.82 mmol) at −5° C. in anhydrous DCM (4 mL) was added tert-butanol (solution in 0.5 mL anhydrous DCM) (81 μL, 0.85 mmol) dropwise over 5 min and the reaction stirred at −5° C. for 15 min. After this time, DIPEA (296 μL, 1.70 mmol) was added dropwise. After 15 min a solution of 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (9) (310 mg, 0.68 mmol) in DCM (1 mL) was added and the reaction was allowed to warm to RT and stirred for 16 h. The reaction was partitioned between water (10 mL) and DCM (20 mL) and the organic washed with 1 M HCl (aq.) (2×20 mL), and brine (10 mL), dried (MgSO4), filtered and solvent removed in vacuo to afford crude product. The residue was purified by silica gel chromatography (40 g, 0-4% MeOH in DCM) to afford tert-butyl (3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrol-2-yl)sulfonylcarbamate (10) (166 mg, 35%) as a colourless oil: m/z 636 (M+H)+ (ES+); 634 (M−H)− (ES−).

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 16 h
  3. customThe reaction was partitioned between water (10 mL) and DCM (20 mL)
  4. washthe organic washed with 1 M HCl (aq.) (2×20 mL), and brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. customto afford crude product
  9. customThe residue was purified by silica gel chromatography (40 g, 0-4% MeOH in DCM)

Sources & evidence

ORD record
ord-90cb7310a9054fc99ab67941682e15bf
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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