Sodium 2-ethylhexanoate → (2R,3R,4S,5R,6E)-7-cyclopentyl-3,4,5-trihydroxy-2-methoxy-N-[(3S)-2-oxo-7-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]hept-6-enamide

HRID 1670416Notes

Reaction equation

HRID 1670416 reaction equation
[CH:1]1(/[CH:6]=[CH:7]/[C@H:8]([C@@H:10]2[O:14][C:13](=[O:15])[C@H:12]([O:16][CH3:17])[C@@H:11]2[OH:18])[OH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:20][C@H:21]1[CH2:27][CH2:26][C:25]2[CH:28]=[C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:30]=[CH:31][C:24]=2[NH:23][C:22]1=[O:38].C(C(CCCC)C([O-])=O)C.[Na+]>C1COCC1>[CH:1]1(/[CH:6]=[CH:7]/[C@@H:8]([OH:9])[C@H:10]([OH:14])[C@@H:11]([OH:18])[C@@H:12]([O:16][CH3:17])[C:13]([NH:20][C@H:21]2[CH2:27][CH2:26][C:25]3[CH:28]=[C:29]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:30]=[CH:31][C:24]=3[NH:23][C:22]2=[O:38])=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 23672331Sodium 2-ethylhexanoateHCID 57463784(3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-oneHCID 67344609(3S)-3-amino-7-phenyl-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one hydrochloride

Product 1

HCID 57463783(2R,3R,4S,5R,6E)-7-cyclopentyl-3,4,5-trihydroxy-2-methoxy-N-[(3S)-2-oxo-7-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]hept-6-enamideYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg of 19 (0.39 mmol), 112.6 mg of 14a (0.39 mmol) and 162 mg of sodium 2-ethylhexanoate (0.98 mmol) in 2.0 ml of THF are successively introduced into a Wheaton tube, with agitation and under an argon atmosphere. The agitation is maintained at AT for 24 h. The reaction medium is directly evaporated to dryness. The crude is chromatographed on a silica cartridge (12 g, eluent EtOAc). 92 mg of expected product Ex5 (white solid) are obtained.

Workup

  1. temperatureThe agitation is maintained at AT for 24 h
  2. customThe reaction medium is directly evaporated to dryness
  3. customThe crude is chromatographed on a silica cartridge (12 g, eluent EtOAc)

Sources & evidence

ORD record
ord-1b8b6117e03245e59d1b710a285ec006
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

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