Methanesulfonyl chloride → HCID 53946344, compound

HRID 1090158Notes

Reaction equation

HRID 1090158 reaction equation
O[CH:2]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27]([C:28]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:7][CH:6]=1)[CH2:3][CH3:4].C1CCN2C(=NCCC2)CC1.CS(Cl)(=O)=O>C(Cl)Cl>[CH:2]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27]([C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:26]=[N:25][N:24]=3)=[CH:15][CH:16]=2)[C:8]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:7][CH:6]=1)=[CH:3][CH3:4]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 14987370HCID 14987370, compound

Product 1

HCID 53946344HCID 53946344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-(1-hydroxypropyl)-1-[2'-(1-triphenylmethyltetrazol-5-yl)biphenyl-4-yl-methyl]pyrrole-2-carboxylate (2.0 g, 3.0 mmol) in methylene chloride (100 ml) at 0° C. was added DBU (2.0 ml, 12.0 mmol) followed by methanesulfonyl chloride (0.7 ml, 9.0 mmol). The mixture was stirred overnight at room temperature whereupon an additional aliquot of DBU (2.0 ml) and methanesulfonyl chloride (0.7 ml) were added and the mixture was allowed to stir an additional 24 hours. The mixture was poured into a separatory funnel and washed with water (3×50 ml) and saturated aqueous sodium bicarbonate solution (50 ml) before being dried (MgSO4), filtered and concentrated. The crude residue was purified by flash chromatography on silica gel (150 g, 10-30% EtOAc/hexanes) to give the title compounds as a mixture of cis/trans isomers (ca. 1/4).

Workup

  1. additionwere added
  2. additionThe mixture was poured into a separatory funnel
  3. washwashed with water (3×50 ml) and saturated aqueous sodium bicarbonate solution (50 ml)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash chromatography on silica gel (150 g, 10-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c1c2b2abcdac440fb35c01198e00b7d3
Source dataset
uspto-grants-1992_01
Patent number
US05081127

Reaction notes

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