allyl (5R,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate → allyl (5R,6S)-2-[(2S,4S)-N-allyloxycarbonyl-2-(1-allyloxycarbonyl-3-pyrazolidinon-5-yl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

HRID 1755729Notes

Reaction equation

HRID 1755729 reaction equation
O(P(O[C:18]1[CH2:19][C@@H:20]2[C@@H:30]([C@H:31]([OH:33])[CH3:32])[C:29](=[O:34])[N:21]2[C:22]=1[C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[CH2:35]([O:38][C:39]([N:41]1[CH2:45][C@@H:44]([SH:46])[CH2:43][C@H:42]1[CH:47]1[N:51]([C:52]([O:54][CH2:55][CH:56]=[CH2:57])=[O:53])[NH:50][C:49](=[O:58])[CH2:48]1)=[O:40])[CH:36]=[CH2:37]>>[CH2:35]([O:38][C:39]([N:41]1[CH2:45][C@@H:44]([S:46][C:18]2[CH2:19][C@@H:20]3[C@@H:30]([C@H:31]([OH:33])[CH3:32])[C:29](=[O:34])[N:21]3[C:22]=2[C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[CH2:43][C@H:42]1[CH:47]1[N:51]([C:52]([O:54][CH2:55][CH:56]=[CH2:57])=[O:53])[NH:50][C:49](=[O:58])[CH2:48]1)=[O:40])[CH:36]=[CH2:37]

Participants

3

Reactant 2

HCID 10624755allyl (5R,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylateHCID 18657913(2S,4S)-N-allyloxycarbonyl-2-(1-allyloxycarbonyl-3-pyrazolidinon-5-yl)-4-mercaptopyrrolidine

Product 1

HCID 67921337allyl (5R,6S)-2-[(2S,4S)-N-allyloxycarbonyl-2-(1-allyloxycarbonyl-3-pyrazolidinon-5-yl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylateYield 65.6%

Procedure

The same procedure as in Example 8-1 was carried out by using allyl (5R,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (195 mg, 0.40 mmol) and (2S,4S)-N-allyloxycarbonyl-2-(1-allyloxycarbonyl-3-pyrazolidinon-5-yl)-4-mercaptopyrrolidine (162 mg, 0.40 mmol) to obtain allyl (5R,6S)-2-[(2S,4S)-N-allyloxycarbonyl-2-(1-allyloxycarbonyl-3-pyrazolidinon-5-yl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (155 mg, yield: 65.4%).

Sources & evidence

ORD record
ord-ec1c472152814e8b84b4da0a9d7219a0
Source dataset
uspto-grants-1995_08
Patent number
US05438054

Reaction notes

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