Diethyl Ether → HCID 101934791, compound

HRID 976997Notes

Reaction equation

HRID 976997 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:18]([O:20]CC=C)=[O:19])=[C:8]([C:10]3[CH:14]=[C:13]([CH3:15])[N:12]([CH2:16][CH3:17])[N:11]=3)[CH2:9][C@H:5]12)[CH3:3].C(C(CCCC)C([O-])=O)C.[Na+:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C>ClCCl.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:18]([O-:20])=[O:19])=[C:8]([C:10]3[CH:14]=[C:13]([CH3:15])[N:12]([CH2:16][CH3:17])[N:11]=3)[CH2:9][C@H:5]12)[CH3:3].[Na+:36]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 11256464HCID 11256464, compoundHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 101934791HCID 101934791, compoundYield 66.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Allyl(5R,6S)-6-[(R)-1-hydroxyethyl]-2-(1-ethyl-5-methylpyrazol-3-yl)carbapen-2-em-3-carboxylate (267 mg) in dichloromethane (3 ml) and ethyl acetate (3 ml) under argon was treated with sodium 2-ethylhexanoate (183 mg), followed by triphenylphosphine (24 mg), followed by tetrakis(triphenylphosphine)palladium(0) (35 mg) and the mixture was stirred for 45 min. Diethyl ether (100 ml) was then added, and after stirring for 90 minutes, the mixture was centrifuged. The residual solid was dried under a stream of argon, and then in a desiccator. The solid was then taken up in water containing sodium chloride and chromatographed on DIAION HP20SS resin, eluting with water, followed by water/THF mixtures; 1%, 2%, and 3%, THF. Fractions were monitored by HPLC, and those containing the product were combined, reduced in volume and freeze-dried to give sodium (5R,6S)-6-[(R)-1-hydroxyethyl]-2-(1-ethyl-5-methylpyrazol-3-yl)carbapen-2-em-3-carboxylate as a solid (168 mg); νmax (KBr) 1761, 1608, 1577, 1381, 1225 cm-1 ; λmax (H2O)/nm 298 (ε/dm3 mol-1 cm-1 8,531); δ (D2O) 1.26 (d, J ca. 6 Hz), 1.27 (d, J ca. 7 Hz) (together 5H), 2.23 (3H, s), 3.17 (2H, approx d, J ca. 9 Hz), 3.44 (1H, dd, J 2.9 & 6.0 Hz), 4.04 (2H, q, J 7.3 Hz), 4.15-4.25 (2H, m), 6.41 (1H, s) ppm.

Workup

  1. stirringafter stirring for 90 minutes
  2. customThe residual solid was dried under a stream of argon
  3. additioncontaining sodium chloride
  4. customchromatographed on DIAION HP20SS resin
  5. washeluting with water
  6. customfreeze-dried

Sources & evidence

ORD record
ord-b5e99c4d19c742a59d4581c2b9be9389
Source dataset
uspto-grants-1997_03
Patent number
US05612477

Reaction notes

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