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

HRID 612293Notes

Reaction equation

HRID 612293 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-[(lR,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-on-6-yl]acetate (4.103 g) in dichloromethane (15ml) and acetone (15 ml) was ring opened with 4-toluenesulphonic acid hydrate (3.33 g) in water (8 ml) and coupled to (R)-2-bromoacetyltetrahydrofuran (2.11 g) in acetone (20 ml) with potassium carbonate (0.687 g) as described in Example 6(b) for the diastereoisomeric mixture. After purification by flash chromatography, the title compound was obtained as a yellow gum (2.618 g, 49%); [α]D -10.7 (c 1.00 CHCl3).

Workup

  1. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-a75800fa0b72465688fa041da2465320
Source dataset
uspto-grants-1999_12
Patent number
US06001997

Reaction notes

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