Triphenylphosphine → HCID 15542667, compound

HRID 1699516Notes

Reaction equation

HRID 1699516 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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:46]([Si:48]([CH2:70][CH3:71])([CH2:68][CH3:69])[O:49][CH2:50][CH2:51][C:52]1[C:53]2[C:62]3[C:61](=[CH:63][CH:64]=1)[S:60](=[O:66])(=[O:65])[NH:59][C:58](=[O:67])[C:57]=3[CH:56]=[CH:55][CH:54]=2)[CH3:47].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)(Cl)Cl>[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:59]3[C:58](=[O:67])[C:57]4[CH:56]=[CH:55][CH:54]=[C:53]5[C:52]([CH2:51][CH2:50][O:49][Si:48]([CH2:68][CH3:69])([CH2:70][CH3:71])[CH2:46][CH3:47])=[CH:64][CH:63]=[C:61]([C:62]=45)[S:60]3(=[O:66])=[O:65])[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=[O:6])[CH:2]=[CH2:3]

Participants

6

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 15542774HCID 15542774, compound

Product 1

HCID 15542667HCID 15542667, 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 7-(2-triethylsilanyloxy-ethyl)-1,1-dioxo-2,3-dihydro-naphtho[1,8-de][1,2]thiazin-3-one (431 mg, 1.1 mmol) in anhydrous tetrahydrofuiran (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]-1-methyl-2-[1,1,3-trioxo-7-(2-triethylsilanyloxy-ethyl)-2,3-dihydro-naphtho[1,8-de][1,2]thiazin-2-ylmethyl]-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-790e47c0d1224f1b8f7b92b3251f6cbf
Source dataset
uspto-grants-2002_02
Patent number
US06346526B1

Reaction notes

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