Dichloromethane → HCID 71619144, compound

HRID 2276823Notes

Reaction equation

HRID 2276823 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[F:13][C:14]([F:64])([F:63])[C:15]([O:24][CH2:25][C:26]([CH2:48][O:49][C:50]([C:59]([F:62])([F:61])[F:60])([C:55]([F:58])([F:57])[F:56])[C:51]([F:54])([F:53])[F:52])([CH2:33][O:34][C:35]([C:44]([F:47])([F:46])[F:45])([C:40]([F:43])([F:42])[F:41])[C:36]([F:39])([F:38])[F:37])[CH2:27][O:28][CH2:29][CH2:30][CH2:31][OH:32])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17].C(Cl)Cl>C1COCC1>[CH3:8][S:9]([O:32][CH2:31][CH2:30][CH2:29][O:28][CH2:27][C:26]([CH2:33][O:34][C:35]([C:36]([F:39])([F:38])[F:37])([C:40]([F:41])([F:42])[F:43])[C:44]([F:47])([F:46])[F:45])([CH2:48][O:49][C:50]([C:51]([F:52])([F:53])[F:54])([C:55]([F:56])([F:57])[F:58])[C:59]([F:60])([F:61])[F:62])[CH2:25][O:24][C:15]([C:16]([F:19])([F:18])[F:17])([C:20]([F:23])([F:22])[F:21])[C:14]([F:63])([F:64])[F:13])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71619143HCID 71619143, compound

Product 1

HCID 71619144HCID 71619144, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (Et3N, 9.6 mL) and methanesulfonyl chloride (5.4 mL, 68.4 mmol) were added to a solution of compound 5 (20.2 g, 23.8 mmol) dissolved in THF (100 mL) and anhydrous CH2Cl2 (200 mL) mixed solvent at 0° C. The reaction mixture was then stirred at room temperature overnight. The reaction was quenched with water and extracted with CH2Cl2. Evaporation through rotary evaporation followed by flash chromatography on silica gel using hexane/EtOAc as the eluent afforded product mesylate 6 (20.8 g, 22.5 mmol, 95% yield) as a colorless oil: 1H NMR (500 MHz, CD3COCD3) δ 4.21 (t, J=7.5 Hz, 2H), 4.11 (s, 6H), 3.48 (t, J=5.0 Hz, 2H), 3.42 (s, 2H), 2.94 (s, 3H), 1.94-1.90 (m, 2H); 13C NMR (126 MHz, CD3COCD3) δ 122.9 (q, J=293.0 Hz), 81.2-81.0 (m), 68.6, 68.5, 67.1, 67.0, 47.7, 37.6, 30.7; 19F NMR (470 MHz, CD3COCD3) δ −71.19 (s); MS (APCI) m/z 927 (M+H)+, 831 (M−OMs)+; HRMS (ESI) calcd for C21H18F27O7S, 927.0342 (M+H)+, 944.0608 [M+NH4]+. found 927.0357, 944.0553, respectively.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with CH2Cl2
  3. customEvaporation
  4. customthrough rotary evaporation

Sources & evidence

ORD record
ord-5d1ad9a3087946bbae3acd2dc241091e
Source dataset
uspto-grants-2015_09
Patent number
US09133114B2

Reaction notes

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