Methylamine → HCID 89681741, compound

HRID 926137Notes

Reaction equation

HRID 926137 reaction equation
Br[CH2:2][C:3]1[C:4]([C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:5]([O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[C:6]2[C:11]([C:12]=1[CH2:13]Br)=[CH:10][CH:9]=[CH:8][CH:7]=2.[CH2:34]([N:36](CC)CC)C.CN>C1COCC1>[C:30]([O:29][C@@H:23]([C:4]1[C:3]2[CH2:2][N:36]([CH3:34])[CH2:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]=1[O:15][S:16]([C:19]([F:21])([F:22])[F:20])(=[O:17])=[O:18])[C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:32])([CH3:31])[CH3:33]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 89681716HCID 89681716, compound

Product 1

HCID 89681741HCID 89681741, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-ethyl 2-(3,4-bis(bromomethyl)-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate (0.1356 g, 0.219 mmol) and triethylamine (61 μL, 0.438 mmol) in anhydrous THF (10 mL) at 0° C. was added a 2M solution of methylamine in THF (109 μL, 0.219 mmol). The reaction mixture was stirred for 1 hour, then stirred overnight at room temperature. LC/MS shows some desired product. Reaction mixture was heated at 45° C. for 1.5 hours, then additional 2M solution of methylamine in THF (109 μL, 0.219 mmol) was added. After 1 hour, 2M solution of methylamine in THF (0.9 mL) was added and stirred for 45 minutes. LC/MS showed no starting material. The reaction mixture was concentrated and purified by flash column chromatography (silica gel, 30 to 100% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C22H27F3NO6S: 490.2. Found: 490.1.

Workup

  1. stirringstirred overnight at room temperature

Sources & evidence

ORD record
ord-c9088726ffc14a0eb17e396b4938a10a
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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