Diisopropylamine → HCID 57314484, compound

HRID 1755717Notes

Reaction equation

HRID 1755717 reaction equation
O(P(O[C:18]1[C@H:19]([CH3:42])[C@H:20]2[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:21]2[C:22]=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])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[NH:43]1[CH:46]([C@@H:47]2[CH2:51][C@H:50]([SH:52])[CH2:49][N:48]2[C:53]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][C:60]([N+:63]([O-:65])=[O:64])=[CH:59][CH:58]=2)=[O:54])[CH2:45][C:44]1=[O:66].C(NC(C)C)(C)C.C(OCC)(=O)C>C(#N)C>[NH:43]1[CH:46]([C@@H:47]2[CH2:51][C@H:50]([S:52][C:18]3[C@H:19]([CH3:42])[C@@H:20]4[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:21]4[C:22]=3[C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=3)=[O:24])[CH2:49][N:48]2[C:53]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][C:60]([N+:63]([O-:65])=[O:64])=[CH:59][CH:58]=2)=[O:54])[CH2:45][C:44]1=[O:66]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 15200286HCID 15200286, compoundHCID 57199442HCID 57199442, compound

Product 1

HCID 57314484HCID 57314484, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
4 °C

Procedure

To a solution of p-nitrobenzyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (110 mg, 0,195 mmol) in acetonitrile (5 ml) was added in a nitrogen stream at -10° C. a solution of (2S,4S)-2-(2-azetidinon-4-yl)-4-mercapto-N-(p-nitrobenzyloxycarbonyl)pyrrolidine diastereomer B (67 mg, 0.191 mmol, compound of Reference Example 3) in acetonitrile (5 ml), and then N,N-diisopropylamine (34 μl, 0.21 mmol) was dropwise added thereto. The mixture was stirred overnight at 4° C. Then, ethyl acetate (50 ml) was added to the reaction solution. This mixture was washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, 3% methanol-chloroform) to obtain p-nitrobenzyl (1R,5S,6S)-2-[(2S,4S)-2-(2-azetidinon-4-yl)-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate diastereomer B (88.5 mg, yield: 68.2%).

Workup

  1. washThis mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89a819aefc3d4a1da450275abb58d101
Source dataset
uspto-grants-1995_08
Patent number
US05438054

Reaction notes

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