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

HRID 1670419Notes

Reaction equation

HRID 1670419 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]=[CH:29][CH:30]=[CH:31][C:24]=2[N:23]([CH3:32])[C:22]1=[O:33].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]=[CH:29][CH:30]=[CH:31][C:24]=3[N:23]([CH3:32])[C:22]2=[O:33])=[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 67345769(S)-3-Amino-1-methyl-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one hydrochloride

Product 1

HCID 57463782(2R,3R,4S,5R,6E)-7-cyclopentyl-3,4,5-trihydroxy-2-methoxy-N-[(3S)-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]hept-6-enamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg of 19 (0.39 mmol), 88.42 mg of 8a (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), and 60 mg of expected product Ex6 (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), and 60 mg of expected product Ex6 (white solid)
  4. customare obtained

Sources & evidence

ORD record
ord-8ce37e0103a543188413b0ced4165e58
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

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