Toluene → HCID 67653950, compound

HRID 1459442Notes

Reaction equation

HRID 1459442 reaction equation
S(Cl)(Cl)=O.[CH2:5]([O:12][C:13]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][C:14]=1[C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:38]N(C)C=O.[C:43]1([CH3:49])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH2:5]([O:12][C:13]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:26][C:14]=1[C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:38][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:43][CH3:49])=[O:24])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 53678558HCID 53678558, compound

Product 1

HCID 67653950HCID 67653950, compoundYield 82%

Procedure

4.6 g (40 mmol) of thionyl chloride dissolved in 12 ml of anhydrous toluene were dropwise added to a suspension of 9.0 g (20 mmol) of 6-{N-[2,5-di(benzyloxy)benzoyl]amino}hexanoic acid (compound of Example 3) in 60 ml of anhydrous toluene and 0.93 g (13 mmol) of anhydrous dimethylformamide at room temperature during 5 minutes stirring. The reaction mixture was stirred at 50° C. for 1 hour then evaporated under reduced pressure to dryness at a temperature below 50° C. The residue obtained was thoroughly triturated with ether, filtered to obtain 7.68 g (82%) of the aimed product, m.p.: 90°-94° C.

Workup

  1. stirringThe reaction mixture was stirred at 50° C. for 1 hour
  2. customthen evaporated under reduced pressure to dryness at a temperature below 50° C
  3. customThe residue obtained
  4. customwas thoroughly triturated with ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ef98fdc3c690482b9305ca66609d10cb
Source dataset
uspto-grants-1998_12
Patent number
US05854250

Reaction notes

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