allyl(1R,5R,6S)-2-(diphenylphosphono)oxy-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate → Allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate

HRID 568257Notes

Reaction equation

HRID 568257 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH2:12][C:13]2[S:17][C:16]3=[CH:18][N:19]=[C:20]([Cl:21])[N:15]3[CH:14]=2)[CH2:10][C@H:9]([S:22]C(=O)C2C=CC=CC=2)[CH2:8]1)=[O:6])[CH:2]=[CH2:3].C1(OP(O[C:48]2[C@H:49]([CH3:65])[C@@H:50]3[C@@H:60]([C@H:61]([OH:63])[CH3:62])[C:59](=[O:64])[N:51]3[C:52]=2[C:53]([O:55][CH2:56][CH:57]=[CH2:58])=[O:54])(OC2C=CC=CC=2)=O)C=CC=CC=1>>[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH2:12][C:13]2[S:17][C:16]3=[CH:18][N:19]=[C:20]([Cl:21])[N:15]3[CH:14]=2)[CH2:10][C@H:9]([S:22][C:48]2[C@H:49]([CH3:65])[C@@H:50]3[C@@H:60]([C@H:61]([OH:63])[CH3:62])[C:59](=[O:64])[N:51]3[C:52]=2[C:53]([O:55][CH2:56][CH:57]=[CH2:58])=[O:54])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 11167930allyl(1R,5R,6S)-2-(diphenylphosphono)oxy-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylateHCID 86756332(3S,5S)-1-Allyloxycarbonyl-3-benzoylthio-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine

Product 1

HCID 131722367Allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylateYield 58.9%

Procedure

The procedure of Example 23-a) is repeated, except that 303.0 mg of (3S,5S)-1-allyloxycarbonyl-3-benzoylthio-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine described in Synthesis Example 23 is used. Thus, 261.0 mg of a mercaptan compound is prepared as a yellow oil. Allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (186.7 mg) is prepared as a colorless amorphous material from this mercaptan and 260.9 mg of allyl(1R,5R,6S)-2-(diphenylphosphono)oxy-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate.

Workup

  1. customdescribed in Synthesis Example 23

Sources & evidence

ORD record
ord-1703b74ba95b4c55b56de63847c7e854
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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