Diethyl Ether → HCID 101934792, compound

HRID 976994Notes

Reaction equation

HRID 976994 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:19]([O:21]CC=C)=[O:20])=[C:8]([C:10]3[CH:14]=[C:13]([CH2:15][CH3:16])[N:12]([CH2:17][CH3:18])[N:11]=3)[CH2:9][C@H:5]12)[CH3:3].C(C(CCCC)C([O-])=O)C.[Na+:37].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:25](=[O:26])[N:6]2[C:7]([C:19]([O-:21])=[O:20])=[C:8]([C:10]3[CH:14]=[C:13]([CH2:15][CH3:16])[N:12]([CH2:17][CH3:18])[N:11]=3)[CH2:9][C@H:5]12)[CH3:3].[Na+:37]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 131719867HCID 131719867, compound

Product 1

HCID 101934792HCID 101934792, compoundYield 66.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Allyl(5R,6S)-6-[(R)-1-hydroxyethyl]-2-(1,5-diethylpyrazol-3-yl)carbapen-2-em-3-carboxylate (267 mg) in dichloromethane (2 ml) and ethyl acetate (2 ml) under argon were treated with sodium 2-ethylhexanoate (135 mg), followed by triphenylphosphine (17.5 mg), followed by tetrakis(triphenylphosphine)palladium(0) (28.3 mg) and the mixture was stirred for 45 min. Diethyl ether (100 ml) was then added, and after stirring for 30 minutes the mixture was centrifuged. The residual solid was washed with diethyl ether, and dried under a stream of argon. The solid was then taken up in a small amount of water and chromatographed on DIAION HP20SS resin, eluting with water, followed by water/THF mixtures; 2%, 3%, 4% and 6% THF. Fractions were monitored by HPLC, and those containing the product were combined, reduced in volume and freeze-dried to give sodium (5R,65)-6-[(R)-1-hydroxyethyl]-2-(1,5-diethylpyrazol-3-yl)carbapen-2-em-3-carboxylate as a solid (169 mg); νmax (KBr) 1752, 1593, 1433, 1382, 1288, and 1258 cm-1 ; λmax (H2O)/nm 298 (ε/dm3 mol-1 cm-1 9,031), 260 (sh) (ε5853); δ (D2O) 1.19 (t, J 7.6 Hz), 1.27 (d, J ca. 6.8 Hz), 1.28 (d, J ca. 7.3 Hz) (together 9H), 2.60 (2H, q, J 7.5 Hz), 3.18 (2H, d, J 9.8 Hz), 3.46 (1H, dd, J 2.7 & 5.9 Hz), 4.05 (2H, q, J 7.2 Hz), 4.14-4.26 (2H, m), 6.48 (1H, s) ppm; [Found (electrospray ms) m/z 342 (MH)+ ].

Workup

  1. stirringafter stirring for 30 minutes the mixture
  2. washThe residual solid was washed with diethyl ether
  3. customdried under a stream of argon
  4. customchromatographed on DIAION HP20SS resin
  5. washeluting with water
  6. customfreeze-dried

Sources & evidence

ORD record
ord-c7aacd16ad16482ea1fd3945c7c1e8d1
Source dataset
uspto-grants-1997_03
Patent number
US05612477

Reaction notes

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