p-Toluenesulfonic acid → HCID 131721510, compound

HRID 612316Notes

Reaction equation

HRID 612316 reaction equation
[OH:1][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]=[CH:26][CH:25]=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].C1(C)C=CC(S(O)(=O)=[O:37])=CC=1.Br[CH2:42][C:43]([C@@H:45]1[C@H:49]([O:50][CH3:51])[C@@H:48]([O:52][CH3:53])[CH2:47][O:46]1)=[O:44].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.ClCCl.O.CC(C)=O>[OH:1][CH:2]([N:15]1[C@H:16]([S:17][CH2:42][C:43]([C@@H:45]2[C@H:49]([O:50][CH3:51])[C@@H:48]([O:52][CH3:53])[CH2:47][O:46]2)=[O:44])[C@H:20]([NH:19][C:18](=[O:37])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]1=[O:22])[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)=[O:4]

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 18396288HCID 18396288, compoundHCID 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 131721510HCID 131721510, compoundYield 42.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

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 (6.0 g, 14.6 mmol) in 50% acetone/dichloromethane (60 ml) was cleaved with 4-toluenesulphonic acid (5.0 g, 26.3 mmol) in water (12 ml). The product was reacted with crude bromide from Example 34 (e) (3.40 g, 13.4 mmol) in acetone (70 ml) followed by potassium carbonate (1.0 g, 7.2 mmol) as described in Example 6 (b). After work-up, the residue was purified by chromatography on silica gel eluting with 50, 70 and 100% ethyl acetate in hexane to yield the title compound (3.40 g, 42%); νmax (CH2Cl2) 3400, 1781, 1735, 1682, 1613 and 1516 cm-1. (Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (625)].

Workup

  1. customAfter work-up, the residue was purified by chromatography on silica gel eluting with 50, 70 and 100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-cadef2564a474037a3ceba1dcad7241d
Source dataset
uspto-grants-1999_12
Patent number
US06001997

Reaction notes

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