2-Ethylhexanoic Acid → Sodium (1S,5R,6S)-6-[1(R)-hydroxy-ethyl]-1-methyl-2-(3-methyl-2,2-dioxo-2,3-dihydro-2-thia-1,3-diaza-cyclopenta[b]naphthalen-1-yl-methyl)-carbapen-2-em-3-carboxylate

HRID 1596730Notes

Reaction equation

HRID 1596730 reaction equation
C(OC([O:7][C@@H:8]([C@H:10]1[C:40](=[O:41])[N:12]2[C:13]([C:34]([O:36]CC=C)=[O:35])=[C:14]([CH2:17][N:18]3[C:22]4=[CH:23][C:24]5[C:29]([CH:30]=[C:21]4[N:20]([CH3:31])[S:19]3(=[O:33])=[O:32])=[CH:28][CH:27]=[CH:26][CH:25]=5)[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[Na+:71].C(OCC)(=O)C.C(C(CCCC)C(O)=O)C>ClCCl.C(OCC)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:7][C@@H:8]([C@H:10]1[C:40](=[O:41])[N:12]2[C:13]([C:34]([O-:36])=[O:35])=[C:14]([CH2:17][N:18]3[C:22]4=[CH:23][C:24]5[C:29]([CH:30]=[C:21]4[N:20]([CH3:31])[S:19]3(=[O:33])=[O:32])=[CH:28][CH:27]=[CH:26][CH:25]=5)[C@H:15]([CH3:16])[C@H:11]12)[CH3:9].[Na+:71]

Participants

9

Reactant 5

HCID 86972-Ethylhexanoic AcidHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 15538053allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methyl-2-(3-methyl-2,2-dioxo-2,3-dihydro-2-thia-1,3-diaza-cyclopenta[b]naphthalen-1-yl-methyl)-carbapen-2-em-3-carboxylateHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 23701550Sodium (1S,5R,6S)-6-[1(R)-hydroxy-ethyl]-1-methyl-2-(3-methyl-2,2-dioxo-2,3-dihydro-2-thia-1,3-diaza-cyclopenta[b]naphthalen-1-yl-methyl)-carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The product from step 1 (52 mg, 0.089 mmol), triphenylphosphine (7 mg, 0.0267 mmol), 0.5M sodium 2-ethyl-hexanoate in ethyl acetate (0.178 mL, 0.089 mmol), 2-ethyl-hexanoic acid (0.014 mL, 0.089 mmol) and tetrakis(triphenylphosphine)palladium(0) (10 mg, 0.0089 mmol) were combined in dichloromethane (1.5 mL). The mixture was stirred at room temperature for 15 minutes, then diluted with ethyl ether (20 mL) and centrifuged. The solid pellet was washed with ether (5 mL) and dried under vacuum to afford the title compound as a white solid.

Workup

  1. washThe solid pellet was washed with ether (5 mL)
  2. customdried under vacuum

Sources & evidence

ORD record
ord-0c869f33f589427081a00a0ff086b28f
Source dataset
uspto-grants-2001_09
Patent number
US06291448B1

Reaction notes

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