(2R,4S)-N-allyloxycarbonyl-2-(2,4-dioxoimidazolidin-5-ylmethyl)-4-tritylthiopyrrolidine → allyl (1R,5S,6S)-2-[(2R,4S)-N-allyloxycarbonyl-2-(2,4-dioxoimidazolidin-5-ylmethyl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 1755746Notes

Reaction equation

HRID 1755746 reaction equation
[CH3:1][CH:2]1[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[C:4]([C:10]([O-:12])=[O:11])=[CH:3]1.[CH2:13]([O:16][C:17]([N:19]1[CH2:23][C@@H:22]([S:24]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:21][C@H:20]1[CH2:44][CH:45]1[NH:49][C:48](=[O:50])[NH:47][C:46]1=[O:51])=[O:18])[CH:14]=[CH2:15]>>[CH2:13]([O:16][C:17]([N:19]1[CH2:23][C@@H:22]([S:24][C:3]2[C@H:2]([CH3:1])[C@@H:6]3[C@@H:7]([C@H:8]([OH:9])[CH3:7])[C:8](=[O:9])[N:5]3[C:4]=2[C:10]([O:12][CH2:3][CH:2]=[CH2:1])=[O:11])[CH2:21][C@H:20]1[CH2:44][CH:45]1[NH:49][C:48](=[O:50])[NH:47][C:46]1=[O:51])=[O:18])[CH:14]=[CH2:15]

Participants

3

Reactant 2

HCID 67750164(2R,4S)-N-allyloxycarbonyl-2-(2,4-dioxoimidazolidin-5-ylmethyl)-4-tritylthiopyrrolidineHCID 1317190691-Methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 131718815allyl (1R,5S,6S)-2-[(2R,4S)-N-allyloxycarbonyl-2-(2,4-dioxoimidazolidin-5-ylmethyl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylateYield 31%

Procedure

The same procedure as in Example 8-1 was carried out by using allyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6-(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (220 mg, 0.440 mmol) and (2R,4S)-N-allyloxycarbonyl-2-(2,4-dioxoimidazolidin-5-ylmethyl)-4-tritylthiopyrrolidine diastereomer B (220 mg, 0.406 mmol, compound of Reference Example 29) to obtain allyl (1R,5S,6S)-2-[(2R,4S)-N-allyloxycarbonyl-2-(2,4-dioxoimidazolidin-5-ylmethyl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate diastereomer B (70 mg, yield: 31%).

Sources & evidence

ORD record
ord-21ed0e29fcee4916a1f8e31c91d1f170
Source dataset
uspto-grants-1995_08
Patent number
US05438054

Reaction notes

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