Triphenylphosphine → HCID 15542665, compound

HRID 1699514Notes

Reaction equation

HRID 1699514 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].[O:27]=[S:28]1(=[O:42])[C:33]2=[CH:34][CH:35]=[CH:36][C:37]3=[CH:38][CH:39]=[CH:40][C:31](=[C:32]23)[C:30](=[O:41])[NH:29]1.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>[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:29]3[C:30](=[O:41])[C:31]4[CH:40]=[CH:39][CH:38]=[C:37]5[CH:36]=[CH:35][CH:34]=[C:33]([C:32]=45)[S:28]3(=[O:42])=[O:27])[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 15542772HCID 15542772, compound

Product 1

HCID 15542665HCID 15542665, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-2-hydroxymethyl-1-methyl-carbapen-2-em-3-carboxylate (64.8 mg, 0.174 mmol), 1,1-dioxo-2,3-dihydro-naphtho[1,8de][1,2]thiazin-3-one (34.5 mg, 0.145 mmol), and triphenylphosphine (46 mg, 0.174 mmol) in anhydrous tetrahydrofuran (2 mL) was cooled in an ice bath and stirred under a nitrogen atmosphere. Diisopropyl azodicarboxylate (0.034 mL, 0.174 mmol) was added and the resulting mixture was stirred at 0-5° C for 10 minutes. The mixture was concentrated under vacuum and the residue was purified by preparative layer chromatography on a 1 mm×20 cm×20 cm silica gel GF plate using 7:3 ethyl acetate-hexanes as the developing solvent. The product band was removed and eluted with ethyl acetate to afford allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methyl-2-(1,1,3-trioxo-2,3-dihydro-naphtho[1,8-de][1,2]thiazin-2-ylmethyl)-carbapen-2-em-3-carboxylate (49 mg) as an oil.

Workup

  1. stirringthe resulting mixture was stirred at 0-5° C for 10 minutes
  2. concentrationThe mixture was concentrated under vacuum
  3. customthe residue was purified by preparative layer chromatography on a 1 mm×20 cm×20 cm silica gel GF plate
  4. customThe product band was removed
  5. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-34f98f9ca10140d590a52c909a3cdf73
Source dataset
uspto-grants-2002_02
Patent number
US06346526B1

Reaction notes

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