Triphenylphosphine → allyl (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-carboxylate

HRID 1596729Notes

Reaction equation

HRID 1596729 reaction equation
[CH2:1]([O:4][C:5]([O:7][C@@H:8]([C@H:10]1[C:25](=[O:26])[N:12]2[C:13]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[C:14]([CH2:17]O)[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=[O:6])[CH:2]=[CH2:3].[CH3:27][N:28]1[C:32]2=[CH:33][C:34]3[C:39]([CH:40]=[C:31]2[NH:30][S:29]1(=[O:42])=[O:41])=[CH:38][CH:37]=[CH:36][CH:35]=3.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.ClCCl.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([O:7][C@@H:8]([C@H:10]1[C:25](=[O:26])[N:12]2[C:13]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[C:14]([CH2:17][N:30]3[C:31]4=[CH:40][C:39]5[C:34]([CH:33]=[C:32]4[N:28]([CH3:27])[S:29]3(=[O:41])=[O:42])=[CH:35][CH:36]=[CH:37][CH:38]=5)[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=[O:6])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11046746allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylateHCID 155380521-Methyl-1,3-dihydro-2-thia-1,3-diaza-cyclopenta[B]naphthalene 2,2-dioxide

Product 1

HCID 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-carboxylateYield 54.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-2-hydroxymethyl-1-methyl-carbapen-2-em-3-carboxylate (60 mg, 0.164 mmol), 1-methyl-1,3-dihydro-2-thia-1,3-diaza-cyclopenta[b]naphthalene 2,2-dioxide (42 mg, 0.180 mmol), and triphenylphosphine (65 mg, 0.246 mmol) in anhydrous tetrahydrofuran (1 mL) was cooled in an ice bath and treated with diisopropyl azodicarboxylate (0.049 mL, 0.246 mmol). The mixture was stirred at 0-5° C. for 30 minutes, then streaked onto two 1 mm ×20 cm×20 cm silica gel GF plates. The plates were developed with 5% ethyl acetate in dichloromethane. The product band was removed and eluted with ethyl acetate to afford allyl (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-carboxylate (52 mg) as an oil.

Workup

  1. customThe product band was removed
  2. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-4bc4e463210c43bd89c8e2a1a358f831
Source dataset
uspto-grants-2001_09
Patent number
US06291448B1

Reaction notes

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