Dichloromethane → HCID 86750491, compound

HRID 975727Notes

Reaction equation

HRID 975727 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH2:9][C@H:8]1[CH2:31][CH2:32][N:33]1[CH:37]=[C:36]([C:38](=[O:40])[NH2:39])[N:35]=[CH:34]1)=[O:6])[CH:2]=[CH2:3].F[C:42](F)(F)S(OC)(=O)=O.[Cl:50]CCl>>[Cl-:50].[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH2:9][C@H:8]1[CH2:31][CH2:32][N+:33]1[CH:37]=[C:36]([C:38](=[O:40])[NH2:39])[N:35]([CH3:42])[CH:34]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 9526Methyl triflateHCID 57259389HCID 57259389, compound

Product 1

HCID 86750491HCID 86750491, compound

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(4-carbamoylimidazol-1-yl)ethyl}-pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.07 g) in dichloromethane (20 ml) was added methyl trifluoromethanesulfonate (1.16 ml) at 0° C. and the solution was stirred for 30 minutes. To the mixture was added a suspension of ion exchange resin, Amberlist A-26 (Cl- type, Trademark, made by Rohm and Haas Co., Ltd.) (10 ml) in dichloromethane (10 ml) and the whole was stirred for 5 minutes. The resin was removed by filtration and washed with a mixture of dichloromethane and methanol (4/1, 50 ml). The filtrate was concentrated in vacuo to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(4-carbamoyl-3-methyl-1-imidazolio)ethyl}pyrrolidin-4yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1azabicyclo[3.2.0]hept-2-ene-2-carboxylate chloride (2.75 g) as a pale yellow solid. This compound was immediately used as the starting compound for the next step.

Workup

  1. additionTo the mixture was added
  2. stirringthe whole was stirred for 5 minutes
  3. customThe resin was removed by filtration
  4. washwashed with a mixture of dichloromethane and methanol (4/1, 50 ml)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-314e7f28c1824ac0bd52e57d2ee0c60e
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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