Acetonitrile → HCID 131730036, compound

HRID 2067716Notes

Reaction equation

HRID 2067716 reaction equation
O(P(OC1C=CC=CC=1)(O[C:11]1[C@H:17]([CH3:18])[C@@H:16]2[N:13]([C:14](=[O:22])[C@@H:15]2[C@H:19]([OH:21])[CH3:20])[C:12]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])=O)C1C=CC=CC=1.C(N([CH:49]([CH3:51])[CH3:50])CC)(C)C.C([S:55][C@@H:56]1[CH2:60][N:59]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[C@H:58]([C:68]([OH:70])=O)[CH2:57]1)(=O)C.[C:71]([O:74]CC)(=O)[CH3:72].C(#[N:79])C>>[CH:68]([C@:58]1([NH:79][CH2:72][C:71]2[O:74][CH:51]=[CH:49][CH:50]=2)[CH2:57][C@H:56]([S:55][C:11]2[C@H:17]([CH3:18])[C@H:16]3[N:13]([C:14](=[O:22])[C@@H:15]3[C@H:19]([OH:21])[CH3:20])[C:12]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH2:60][N:59]1[C:61]([O:63][C:64]([CH3:65])([CH3:66])[CH3:67])=[O:62])=[O:70]

Participants

6

Reactant 5

HCID 6342Acetonitrile2×HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 15200286HCID 15200286, compoundHCID 594363011-(1,1-Dimethylethyl) (2S,4S)-4-(acetylthio)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 131730036HCID 131730036, compoundYield 73.1%

Conditions

Temperature
0 °C

Procedure

A solution of 17.9 g (30 mmol) of p-nitrobenzyl(4R,5S,6S)-3-(diphenoxy-phosphoryloxy)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate in 150 ml of acetonitrile was added into a flask and the reaction mixture was cooled below −10° C. Then diisopropylethylamine (8 mL) and a solution of the intermediate (I-1) prepared by Intermediate Example 1 (10.1 g, 31 mmol) in 100 mL of acetonitrile were added and the reaction mixture was stirred at 0° C. for 15 hours. After the completion of the reaction, ethyl acetate (400 mL) was added to the reaction mixture for dilution and the mixture was washed successively with water and saturated brine. The organic layer was dried and concentrated to give 14.7 g (yield: 73.1%) of p-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-formyl[[furan-2-ylmethyl]amino]-1-(tert-butoxycarbonyl)pyrrolidine-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate, which is the intermediate II-1.

Workup

  1. temperaturethe reaction mixture was cooled below −10° C
  2. additionwere added
  3. additionwas added to the reaction mixture for dilution
  4. washthe mixture was washed successively with water and saturated brine
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8e7a9f9c712f491ab400bbc044f953b8
Source dataset
uspto-grants-2012_10
Patent number
US08293895B2

Reaction notes

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