Diisopropylethylamine → HCID 10531203, compound

HRID 1492322Notes

Reaction equation

HRID 1492322 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.C(N(CC)C(C)C)(C)C.Cl.Cl.[OH:54][CH2:55][CH2:56][N:57]1[CH2:62][CH2:61][CH:60]([C@@H:63]2[CH2:67][C@H:66]([SH:68])[CH2:65][NH:64]2)[CH2:59][CH2:58]1>C(#N)C>[OH:40][C@@H:38]([C@H:37]1[C:36](=[O:41])[N:21]2[C:22]([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])=[C:18]([S:68][C@@H:66]3[CH2:65][NH:64][C@H:63]([CH:60]4[CH2:59][CH2:58][N:57]([CH2:56][CH2:55][OH:54])[CH2:62][CH2:61]4)[CH2:67]3)[C@H:19]([CH3:42])[C@H:20]12)[CH3:39]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15200286HCID 15200286, compoundHCID 131718794HCID 131718794, compound

Product 1

HCID 10531203HCID 10531203, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of p-nitrobenzyl (1R, 5S, 6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (8.92 g, 15 mmol) in acetonitrile (600 ml), N,N-diisopropylethylamine (10.7 ml, 61.5 mmol) was added under cooling with ice and (2S, 4S)-2-[N-(2-hydroxyethyl)piperidin-4-yl]-4-mercaptopyrrolidine dihydrochloride (4.80 g, 15.8 mmol) was further added in limited amount. After the mixture was stirred at the same temperature for 19 hours, the reaction solution was concentrated to a volume of 300 ml and stirred under cooling with ice for 2 hours. Precipitates were collected by filtration and washed with acetonitrile, followed by drying to obtain p-nitrobenzyl (1R, 5S, 6S)-6-[(R)-1-hydroxyethyl]-2-[(2S, 4S)-2-[N-(2-hydroxyethyl)piperidin-4-yl]pyrrolidin-4-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate (4.77g, yield: 55.4%).

Workup

  1. additionwas further added in limited amount
  2. concentrationthe reaction solution was concentrated to a volume of 300 ml
  3. stirringstirred
  4. temperatureunder cooling with ice for 2 hours
  5. customPrecipitates
  6. filtrationwere collected by filtration
  7. washwashed with acetonitrile
  8. customby drying

Sources & evidence

ORD record
ord-09305f2b78b3445dac85dbc611bd740d
Source dataset
uspto-grants-1994_12
Patent number
US05373002

Reaction notes

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