tert-Butanol → HCID 59737387, compound

HRID 1907771Notes

Reaction equation

HRID 1907771 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13]C(=O)OC(C)(C)C.[CH3:21][O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1.[CH3:32][C:33]([OH:36])([CH3:35])[CH3:34].[S:37](Cl)([N:40]=[C:41]=[O:42])(=[O:39])=[O:38].CCN(CC)CC>C(Cl)Cl>[CH3:21][O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:1][C:2]2[CH:7]=[C:6]([C:8]3[S:9][CH:10]=[CH:11][CH:12]=3)[CH:5]=[CH:4][C:3]=2[NH:13][S:37]([NH:40][C:41](=[O:42])[O:36][C:33]([CH3:35])([CH3:34])[CH3:32])(=[O:39])=[O:38])=[O:28])=[CH:25][CH:24]=1

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 59737387HCID 59737387, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Starting from compound 4 and 4-methoxybenzoyl chloride the compound 445 was synthesized following the general procedure K and G. Then, t-BuOH (0.08 mL, 0.80 mmol) was added dropwise to a solution at 0° C. of sulfurisocyanatidic chloride (0.07 mL, 0.80 mmol) in DCM (20 mL) and stirred for 20 min. A solution of compound 445 (260 mg, 0.80 mmol) in DCM (2 mL) and Et3N (0.3 mL, 2.40 mmol) was added, stirred at room temperature for 18 h, quenched with water, extracted 3 times with DCM, dried over MgSO4 and concentrated. The residue was purified by flash chromatography using 5% MeOH in DCM as an eluent to afford the title compound 446 (365 mg, 90%) as a white solid.

Workup

  1. customwas synthesized
  2. stirringstirred at room temperature for 18 h
  3. customquenched with water
  4. extractionextracted 3 times with DCM
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0868e96f46a44fbd9da41973c6205206
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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