Potassium Carbonate → 4-Methoxybenzyl (6R,7R)-7-Amino-3-((R)-tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate

HRID 376581Notes

Reaction equation

HRID 376581 reaction equation
O[CH:2]([N:15]1[C:21](=[O:22])[C@@H:20]2[C@H:16]1[S:17][C:18]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=CC=1)=[N:19]2)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:4].O.C1(C)C=CC(S(O)(=O)=[O:38])=CC=1.BrCC([C@H]1CCCO1)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CC(C)=O.O>[NH2:19][C@@H:20]1[C:21](=[O:22])[N:15]2[C:2]([C:3]([O:5][CH2:6][C:7]3[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=3)=[O:4])=[C:23]([C@H:24]3[CH2:29][CH2:28][CH2:27][O:38]3)[CH2:18][S:17][C@H:16]12

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 111948672-Bromo-1-[(2R)-tetrahydro-2-furanyl]-ethanoneHCID 536561234-Methoxybenzyl (RS)-2-hydroxy-2-[(lR,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0)hept-2-en-7-on-6-yl]acetate

Product 1

HCID 538410274-Methoxybenzyl (6R,7R)-7-Amino-3-((R)-tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzyl (RS)-2-hydroxy-2-[(1R,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-on-6-yl]acetate (4.103g) in dichloromethane (15ml) and acetone (15ml) was ring opened with 4-toluenesulphonic acid hydrate (3.33g) in water (8ml) and coupled to (R)-2-bromoacetyltetrahydrofuran (2.11g) in acetone (20ml) with potassium carbonate (0.687g) as described in Example 6(b) for the diastereoisomeric mixture. After purification by flash chromatography, the title compound was obtained as a yellow gum (2.618g, 49%); [α]D -10.7 (c 1.00 CHCl3).

Workup

  1. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-24bb69f6ad8d4a45a71b0f4717ca621d
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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