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

HRID 1670438Notes

Reaction equation

HRID 1670438 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[C:27](=[O:28])[NH:26][C:25]2[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:30][CH:31]=[CH:32][C:24]=2[O:23][CH2:22]1.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[C:27](=[O:28])[NH:26][C:25]3[C:29]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[CH:30][CH:31]=[CH:32][C:24]=3[O:23][CH2:22]2)=[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 67328140(3S)-3-amino-6-phenyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride

Product 1

HCID 57617784(2R,3R,4S,5R,6E)-7-cyclopentyl-3,4,5-trihydroxy-2-methoxy-N-[(3S)-4-oxo-6-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

53 mg of 32 (207 μmol), 60 mg of 44 (207 μmol), 86 mg of sodium 2-ethylhexanoate (0.52 mmol) in 1 mL of THF are successively introduced into a Wheaton tube, with stirring and under an argon atmosphere. The stirring is maintained at RT for 24 h. The reaction medium is concentrated to dryness. The residues are chromatographed on a silica cartridge (4 g, eluent AcOEt). 45 mg of expected product Ex17 (cream-coloured solid) are recovered.

Workup

  1. concentrationThe reaction medium is concentrated to dryness
  2. customThe residues are chromatographed on a silica cartridge (4 g, eluent AcOEt)
  3. custom45 mg of expected product Ex17 (cream-coloured solid) are recovered

Sources & evidence

ORD record
ord-f9156c996ed3429dad8883729e09ff20
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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