Hydrochloric Acid → Allyl (5R,6S)-2-[(3S,5S)-N-(allyloxycarbonyl)-5-(1-naphthylmethyl)pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate
Reaction equation
[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@H:7]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[CH2:6]1)(=O)[CH3:2].O(P(OC1C[C@@H:46]2[C@@H:56]([C@H:57]([OH:59])[CH3:58])[C:55](=[O:60])[N:47]2[C:48]=1[C:49]([O:51][CH2:52][CH:53]=[CH2:54])=[O:50])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[OH-].[Na+].Cl.C(N(CC)C(C)C)(C)C>>[CH2:13]([O:12][C:10]([N:8]1[C@@H:7]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[CH2:6][C@H:5]([S:4][C:1]2[CH2:2][C@@H:46]3[C@@H:56]([C@H:57]([OH:59])[CH3:58])[C:55](=[O:60])[N:47]3[C:48]=2[C:49]([O:51][CH2:52][CH:53]=[CH2:54])=[O:50])[CH2:9]1)=[O:11])[CH:14]=[CH2:15]Participants
6
Reactant 5
Product 1
Procedure
Allyl (5R,6S)-2-[(3S,5S)-N-(allyloxycarbonyl)-5-(1-naphthylmethyl)pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (633 mg, yield: 70.1%) was prepared as a yellow powder, from (2R,4S)-4-acetylthio-N-allyloxycarbonyl-2-(1-naphthylmethyl)pyrrolidine (610 mg, 1.53 mmol), allyl (5R,6S)-2-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (743 mg, 1.53 mmol), 1N aqueous sodium hydroxide (1.8 ml, 1.8 mmol), 1N aqueous hydrochloric acid (1.8 ml, 1.8 mmol) and N,N-diisopropylethylamine (800 μl, 4.59 mmol), in the same manner as in Example 135-1.
Sources & evidence
- ORD record
- ord-508070e9327647e599d6aa0523a669d4
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05707987
Reaction notes
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