(S)-7-Amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one hydrochloride → (2R,3R,4S,5R,6E)-7-cyclopentyl-2-ethoxy-3,4,5-trihydroxy-N-[(3S)-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide

HRID 1670445Notes

Reaction equation

HRID 1670445 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][CH2:17][CH3:18])[C@@H:11]2[OH:19])[OH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:21][C@@H:22]1[C:28](=[O:29])[NH:27][C:26]2[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=2[O:24][CH2:23]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:19])[C@@H:12]([O:16][CH2:17][CH3:18])[C:13]([NH:21][C@@H:22]2[C:28](=[O:29])[NH:27][C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[O:24][CH2:23]2)=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 18599716(S)-7-Amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one hydrochlorideHCID 23672331Sodium 2-ethylhexanoateHCID 67329167(3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-3-ethoxy-4-hydroxydihydrofuran-2(3H)-one

Product 1

HCID 57617795(2R,3R,4S,5R,6E)-7-cyclopentyl-2-ethoxy-3,4,5-trihydroxy-N-[(3S)-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

110 mg of 52 (407 μmol), 87 mg of 4 (407 μmol) and 169 mg of sodium 2-ethylhexanoate (1.02 mmol) in 2 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 (8 g, eluent AcOEt). 75 mg of expected product Ex20 are recovered.

Workup

  1. concentrationThe reaction medium is concentrated to dryness
  2. customThe residues are chromatographed on a silica cartridge (8 g, eluent AcOEt)
  3. custom75 mg of expected product Ex20 are recovered

Sources & evidence

ORD record
ord-3e4d5b02dbdc4f44942f20ee032d85f0
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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