Triethylamine → HCID 86661964, compound

HRID 82897Notes

Reaction equation

HRID 82897 reaction equation
[F:1][C:2]([F:17])([S:13](F)(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].CCN(CC)CC.[CH2:25]([CH:32]1[C:40]2[C:35](=[CH:36][C:37]([F:42])=[C:38]([OH:41])[CH:39]=2)[CH2:34][CH:33]1[NH:43][C:44](=[O:48])[O:45][CH2:46][CH3:47])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[F:1][C:2]([F:17])([S:13]([O:41][C:38]1[CH:39]=[C:40]2[C:35](=[CH:36][C:37]=1[F:42])[CH2:34][CH:33]([NH:43][C:44]([O:45][CH2:46][CH3:47])=[O:48])[CH:32]2[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 66741509ethyl 1-benzyl-5-fluoro-6-hydroxy-2,3-dihydro-1H-inden-2-ylcarbamate

Product 1

HCID 86661964HCID 86661964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Perfluorobutanesulfonyl fluoride (0.392 ml, 2.004 mmol) and Et3N (0.419 ml, 3.01 mmol) in abs. dichloromethane (10 ml) was added dropwise to the intermediate ethyl 1-benzyl-5-fluoro-6-hydroxy-2,3-dihydro-1H-inden-2-ylcarbamate (330 mg, 1.002 mmol), dissolved in dichloromethane and stirred at room temperature over night. Evaporated and purified by flash silica gel chromatography on 12 g SiO2-cartridge using dichloromethane to afford 3-benzyl-2-(ethoxycarbonylamino)-6-fluoro-2,3-dihydro-1H-inden-5-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate as a yellow product. M=389 mg (63%)

Workup

  1. customEvaporated
  2. custompurified by flash silica gel chromatography on 12 g SiO2-cartridge

Sources & evidence

ORD record
ord-c74c5899f78b491ca40717851b0ce2b6
Source dataset
uspto-grants-2014_09
Patent number
US08846743B2

Reaction notes

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