Chloromethyl Methyl Ether → HCID 22671944, compound

HRID 1006554Notes

Reaction equation

HRID 1006554 reaction equation
[C:1]([CH2:4][N:5]([S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:29])=[O:28])[C:6]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:7]=1[O:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)([OH:3])=[O:2].C1(S(NC2C=CC(C(F)(F)F)=C[C:47]=2[O:48][CH2:49]C2C=CC(C(OC)=O)=CC=2)(=O)=O)C=CC=CC=1.COCCl.C(N(CC)CC)C>CN(C=O)C.O>[CH3:47][O:48][CH2:49][O:2][C:1]([CH2:4][N:5]([S:27]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)(=[O:28])=[O:29])[C:6]1[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:19][C:7]=1[O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:17][CH:18]=1)=[O:3]

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 12017680HCID 12017680, compoundHCID 22672008HCID 22672008, compound

Product 1

HCID 22671944HCID 22671944, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-[2-(N-carboxymethyl-phenylsulfonylamino)-5-trifluoromethyl-phenoxymethyl]benzoic acid (446 mg) prepared by the same procedure as Example 17→Example 2 by using methyl 4-(2-phenylsulfonylamino-5-trifluoromethylphenoxymethyl)benzoate (prepared in Example 15) was dissolved in DMF (5 ml). To the solution, methoxymethyl chloride (160 μl) and triethylamine (300 μl) were added dropwise. The mixture was stirred for 2 hours at room temperature. Water was added thereto. The mixture was extracted with ethyl acetate, washed, dried over, filtered and concentrated to give the title compound (476 mg) having the following physical data.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed
  3. customdried over,
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-816380e50da14783bc3e99ee8dc4d4be
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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