Hydrochloric Acid → HCID 131718793, compound

HRID 1492321Notes

Reaction equation

HRID 1492321 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C@H:7]([CH2:23][C@H:24]2[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[C@H:26]([CH2:42][OH:43])[CH2:25]2)[CH2:6]1)(=O)C.[OH-:44].[Na+].Cl.[Cl-].[Na+].O(P(O[C:66]1[C@H:67]([CH3:90])[C@H:68]2[C@@H:85]([C@H:86](O)[CH3:87])[C:84](=[O:89])[N:69]2[C:70]=1[C:71]([O:73][CH2:74][C:75]1[CH:80]=[CH:79][C:78]([N+:81]([O-:83])=[O:82])=[CH:77][CH:76]=1)=[O:72])(OC1C=CC=CC=1)=O)C1C=CC=CC=1>C(Cl)Cl.CO>[OH:44][C@@H:86]([C@H:85]1[C:84](=[O:89])[N:69]2[C:70]([C:71]([O:73][CH2:74][C:75]3[CH:76]=[CH:77][C:78]([N+:81]([O-:83])=[O:82])=[CH:79][CH:80]=3)=[O:72])=[C:66]([S:4][C@@H:5]3[CH2:9][NH:8][C@H:7]([CH2:23][C@H:24]4[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]5[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=5)=[O:30])[C@H:26]([CH2:42][OH:43])[CH2:25]4)[CH2:6]3)[C@H:67]([CH3:90])[C@H:68]12)[CH3:87]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 15200286HCID 15200286, compoundHCID 57319250HCID 57319250, compound

Product 1

HCID 131718793HCID 131718793, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(2R, 4S)-4-acetylthio-2-[(2S,4R)-2-hydroxymethyl-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-4-ylmethyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine (150 mg, 0.24 mmol) was dissolved in a solution comprising methylene chloride (0.5 ml) and methanol (1.5 ml). A 2N sodium hydroxide aqueous solution (0.18 ml, 0.36 mmol) was dropwise added under cooling with ice in a nitrogen stream, and the reaction mixture solution was stirred for 20 minutes. After a 6N hydrochloric acid (0.06 ml, 0.36 mmol) was added to the reaction solution, the solution was poured into a saturated sodium chloride aqueous solution, then extracted with methylene chloride, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. By using the compound thus obtained and p-nitrobenzyl (1R, 5S, 6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (130 mg, 0.22 mmol), the same procedure as in Example 1-1) was carried out to obtain p-nitrobenzyl (1R, 5S, 6S)-6-[(R)-1-hydroxyethyl]-2-[(2R, 4S)-2-[(2S, 4R)-2-hydroxymethyl-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-4-ylmethyl]pyrrolidin-4-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate (129 mg, yield: 58%).

Workup

  1. temperatureunder cooling with ice in a nitrogen stream
  2. extractionextracted with methylene chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthus obtained

Sources & evidence

ORD record
ord-12a58a65c92e4a599f97e34de251d109
Source dataset
uspto-grants-1994_12
Patent number
US05373002

Reaction notes

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