tert-Butanol → HCID 123569579, compound

HRID 2370599Notes

Reaction equation

HRID 2370599 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([CH3:15])([CH3:14])[N:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH2:28][C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])[C:9]2=[O:36])=[CH:4][C:3]=1[CH3:37].CCN(CC)CC.Cl[S:46]([N:49]=[C:50]=[O:51])(=[O:48])=[O:47].[CH3:52][C:53]([OH:56])([CH3:55])[CH3:54]>C(Cl)Cl>[CH3:14][C:11]1([CH3:15])[C:12](=[O:13])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:46]([NH:49][C:50](=[O:51])[O:56][C:53]([CH3:55])([CH3:54])[CH3:52])(=[O:48])=[O:47])=[C:3]([CH3:37])[CH:4]=2)[C:9](=[O:36])[N:10]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH2:28][C:29]([F:35])([F:34])[C:30]([F:33])([F:31])[F:32]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 46945366HCID 46945366, compound2×

Product 1

HCID 123569579HCID 123569579, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of the compound of Example 25 (612 mg, 1.1 mmole) and Et3N (0.19 ml, 1.33 mmole) in anhydrous CH2Cl2 (30 ml) is stirred at 0° C. Then a solution of chlorosulphonyl isocyanate (0.11 ml, 1.22 mmole) in anhydrous CH2Cl2 (10 ml), cooled down to 0° C., is completed with t-BuOH (0.12 ml, 1.22 mmole) before being added rapidly to the solution of the compound of Example 25. The mixture is stirred for 30 min at 0° C. followed by 1 hour and a half at 23° C. The reaction medium is then washed successively with water (2×100 ml), a saturated aqueous solution of NaHCO3 (50 ml) and salt water (50 ml). The organic solution is dried over Na2SO4, filtered and concentrated to dryness. The evaporation residue is purified on a silica column (eluent: Heptane/AcOEt: 1/0 to 6/4). The expected compound is obtained in the form of a white solid with a yield of 85%. Melting point 122-124° C.

Workup

  1. waitfollowed by 1 hour
  2. customat 23° C
  3. washThe reaction medium is then washed successively with water (2×100 ml)
  4. dry with materialThe organic solution is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe evaporation residue is purified on a silica column (eluent: Heptane/AcOEt: 1/0 to 6/4)

Sources & evidence

ORD record
ord-fad53deae8da46a6aa6281320620ad34
Source dataset
uspto-grants-2014_04
Patent number
US08710091B2

Reaction notes

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