Tetrahydrofuran → HCID 131723117, compound

HRID 1699538Notes

Reaction equation

HRID 1699538 reaction equation
C(OC(O[C@@H]([C@H:10]1[C:25](=[O:26])[N:12]2[C:13]([C:19]([O:21][CH2:22][CH:23]=C)=[O:20])=[C:14]([CH2:17]O)[C@H:15]([CH3:16])[C@H:11]12)C)=O)C=C.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:32]=CC=C[CH:28]=1.[C:46]1([C:52]2[C:61]3[C:56](=[CH:57][CH:58]=[C:59]([CH2:62][CH2:63][O:64][Si:65]([CH2:70][CH3:71])([CH2:68][CH3:69])[CH2:66][CH3:67])[CH:60]=3)[S:55](=[O:73])(=[O:72])[NH:54][N:53]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.N([C:82]([O:84]C(C)C)=[O:83])=NC(OC(C)C)=O.[O:88]1CCCC1>C(Cl)(Cl)Cl>[CH2:28]([O:83][C:82]([O:84][C@@H:22]([O:21][C:19]([C:13]1[N:12]2[C:25](=[O:26])[CH2:10][C@H:11]2[CH:15]([CH3:16])[C:14]=1[CH2:17][N:54]1[N:53]=[C:52]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:61]2[C:56](=[CH:57][CH:58]=[C:59]([CH2:62][CH2:63][O:64][Si:65]([CH2:68][CH3:69])([CH2:70][CH3:71])[CH2:66][CH3:67])[CH:60]=2)[S:55]1(=[O:72])=[O:73])=[O:20])[CH3:23])=[O:88])[CH:27]=[CH2:32]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11046746allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylateHCID 18319501HCID 18319501, compound

Product 1

HCID 131723117HCID 131723117, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-2-hydroxymethyl-1-methyl-carbapen-2-em-3-carboxylate (365 mg, 1.0 mmol), triphenylphosphine (315 mg, 1.2 mmol), and 4-phenyl-6-(2-triethylsilanyloxy-ethyl)-2H-1-thia-2,3-diaza-naphthalene 1,1-dioxide (458mg, 1.1 mmol) in anhydrous tetrahydrofuran (7 mL) is cooled in an ice-bath and stirred under a nitrogen atmosphere while diisopropyl azodicarboxylate (0.24 mL, 1.2 mmol) is added dropwise over a few minutes. The resulting solution is stirred in the cold for 30 minutes, then diluted with chloroform, washed with 5% aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered and evaporated under vacuum. The residue is purified by silica gel flash chromatography, eluting with hexane-ethyl acetate, to afford allyl (1S,5R,6S)-6-[(1(R)-allyloxycarbonyloxy-ethyl]-2-[1,1-dioxo-4-phenyl-6-(2-triethylsilanyloxy-ethyl)-2H-1-thia-2,3-diaza-naphthalen-2-ylmethyl]-1-methyl-carbapen-2-em-3-carboxylate.

Workup

  1. additionis added dropwise over a few minutes
  2. washwashed with 5% aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue is purified by silica gel flash chromatography
  7. washeluting with hexane-ethyl acetate

Sources & evidence

ORD record
ord-a8838effeba74502b60c99e37ec31342
Source dataset
uspto-grants-2002_02
Patent number
US06346525B1

Reaction notes

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