Sodium 2-ethylhexanoate → (2R,3R,4S,5R,6E)-7-cyclopentyl-N-[(3S)-1,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]-3,4,5-trihydroxy-2-methoxyhept-6-enamide

HRID 1670429Notes

Reaction equation

HRID 1670429 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])[N:26]([CH3:29])[C:25]2[CH:30]=[CH:31][CH:32]=[CH:33][C:24]=2[N:23]([CH3:34])[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])[N:26]([CH3:29])[C:25]3[CH:30]=[CH:31][CH:32]=[CH:33][C:24]=3[N:23]([CH3:34])[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 67329118(3S)-3-amino-1,5-dimethyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one hydrochloride

Product 1

HCID 57617735(2R,3R,4S,5R,6E)-7-cyclopentyl-N-[(3S)-1,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]-3,4,5-trihydroxy-2-methoxyhept-6-enamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

208 mg of 32 (852 μmol), 198 mg of 18 (0.712 mmol) and 473 mg of sodium 2-ethylhexanoate (2.848 mmol) in 5 mL of THF are successively introduced into a 25 mL round-bottomed flask, with stirring and under an argon atmosphere. The stirring is maintained at RT for 2 days. The mixture is concentrated under vacuum. The crude product is chromatographed on a silica cartridge [50 g, eluent AcOEt/AcOEt-isopropanol (50/50), in an AcOEt-isopropanol (50/50) gradient: 0 to 30%]). 172 mg of expected product Ex15 are recovered.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. customThe crude product is chromatographed on a silica cartridge [50 g, eluent AcOEt/AcOEt-isopropanol (50/50)
  3. custom172 mg of expected product Ex15 are recovered

Sources & evidence

ORD record
ord-b8afad34d2cc4d1fb9b01845eb942a87
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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