2-Dimethylaminopyridine → HCID 68914455, compound

HRID 870379Notes

Reaction equation

HRID 870379 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([C@H:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=2)[CH2:12]1)[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].CN(C1C=CC=CN=1)C.[F:32][C:33]([F:46])([F:45])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>O1CCCC1>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:8][CH2:9][CH3:10])[C@H:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:21][S:41]([C:38]3[CH:37]=[CH:36][C:35]([CH2:34][C:33]([F:32])([F:45])[F:46])=[CH:40][CH:39]=3)(=[O:43])=[O:42])[CH:17]=2)[CH2:12]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 53628607883146-03-0HCID 68914769HCID 68914769, compound

Product 1

HCID 68914455HCID 68914455, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

((S)-6-Amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-carbamic acid tert-butyl ester (720 mg, 2.37 mmol) was dissolved in tetrahydrofurane (50 ml). Then, dimethylamino pyridine (100 mg, 0.82 mmol) and 4-(2,2,2-trifluoro-ethyl)benzenesulfonyl chloride (761 mg, 2.37 mmol) were added and the reaction mixture was stirred for 30 minutes at room temperature. The solvent was evaporated under reduced pressure, the residue treated with water and diethyl ether. The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give the crude product (1.22 g, 95% purity, 93% yield).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue treated with water and diethyl ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-4a90f03b72ff478db7a53dcf37745e63
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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