Methanesulfonate → HCID 19013009, compound

HRID 1729541Notes

Reaction equation

HRID 1729541 reaction equation
CS(O[CH2:6][CH:7]1[CH2:11][N:10]([C:12]([OH:14])=[O:13])[C:9]2[CH:15]=[C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]3[NH:18][CH:19]=[C:20]([CH3:22])[C:21]=3[C:8]1=2)(=O)=O.S([O-])(=O)(=O)C.[Cl-:36].[Li+]>CN(C=O)C>[Cl:36][CH2:6][CH:7]1[CH2:11][N:10]([C:12]([OH:14])=[O:13])[C:9]2[CH:15]=[C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]3[NH:18][CH:19]=[C:20]([CH3:22])[C:21]=3[C:8]1=2

Participants

5

Reactant 3

HCID 85257MethanesulfonateHCID 433294Lithium ChlorideHCID 53635860HCID 53635860, compound

Product 1

HCID 19013009HCID 19013009, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200mg (0.29 mmol max) of the product of step 3A, 1,1-dimethylethyl ester of 1-(methanesulfonyloxymethyl) -1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid, the crude mesylate, is stirred under nitrogen at 80° C. in 3 ml DMF and 40 mg lithium chloride for 25 minutes, when TLC shows the reaction to be complete. The reaction mixture is cooled to room temperature, and partitioned between methylene chloride and water. The layers are separated and the aqueous layer reextracted with methylene chloride. The organic layers are combined, dried over sodium sulfate and evaporated under high vacuum. The crude product is chromatographed over 10 g silica gel, eluting with ethyl acetatehexane (20:80). Fraction of 5 ml are collected and the product found by TLC in fractions 7-17, which upon combining and evaporating yield compound 7, 1,1-dtmethylethyl ester of 1-(chloromethyl) -1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2 H)-carboxylic acid.

Workup

  1. customthe reaction
  2. custompartitioned between methylene chloride and water
  3. customThe layers are separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated under high vacuum
  6. customThe crude product is chromatographed over 10 g silica gel
  7. washeluting with ethyl acetatehexane (20:80)
  8. customFraction of 5 ml are collected
  9. customevaporating

Sources & evidence

ORD record
ord-657cc93aac2348bbbeea3d99eaa1365e
Source dataset
uspto-grants-1994_07
Patent number
US05332837

Reaction notes

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