Triphenylphosphine → allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-2-(2,2-dioxo-2,3-dihydro-benzo [c]isothiazol-1-yl-methyl)-1-methyl-carbapen-2-em-3-carboxylate

HRID 1596728Notes

Reaction equation

HRID 1596728 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].[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[CH2:29][S:28]1(=[O:37])=[O:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=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:27]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[CH2:29][S:28]3(=[O:36])=[O:37])[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=[O:6])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11046746allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylateHCID 155360091,3-Dihydro-2,1-benzisothiazole 2,2-dioxide

Product 1

HCID 15538048allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-2-(2,2-dioxo-2,3-dihydro-benzo [c]isothiazol-1-yl-methyl)-1-methyl-carbapen-2-em-3-carboxylateYield 41.5%

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)-allyloxycarbonyloxyethyl]-2-hydroxymethyl-1-methyl-carbapen-2-em-3-carboxylate (25.5 mg, 0.07 mmol), 1,3-dihydro-benzo[c]isothiazole 2,2-dioxide (13 mg, 0.077 mmol), and triphenylphosphine (28 mg, 0.105 mmol) in anhydrous tetrahydrofuran (0.4 mL) was cooled in an ice bath and treated with diethyl azodicarboxylate (0.017 mL, 0.105 mmol). The mixture was stirred at 0-5° C. for 30 minutes, then streaked onto a 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]-2-(2,2-dioxo-2,3-dihydro-benzo [c]isothiazol-1-yl-methyl)-1-methyl-carbapen-2-em-3-carboxylate (15 mg) as an oil.

Workup

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

Sources & evidence

ORD record
ord-ca7ab509396b42bdb5862002987512fd
Source dataset
uspto-grants-2001_09
Patent number
US06291448B1

Reaction notes

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