Cromolyn → 2-[5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoyloxy]-1,3-bis-(2-carboxychromon-5-yloxy)propane

HRID 990014Notes

Reaction equation

HRID 990014 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:11]([C:12](=[O:14])[CH:13]=1)=[C:10]([O:15][CH2:16][CH:17]([OH:34])[CH2:18][O:19][C:20]1[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=1[C:22](=[O:33])[CH:23]=[C:24]([C:30]([OH:32])=[O:31])[O:25]3)[CH:9]=[CH:8][CH:7]=2)([OH:3])=[O:2].[C:35]([NH:54][C@H:55]([C:59]([O:61][CH2:62][CH:63]([CH2:70][O:71][C:72](=[O:90])[CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH3:89])[CH2:64][CH2:65][CH2:66][C:67](O)=[O:68])=[O:60])[CH:56]([CH3:58])[CH3:57])([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CN(C1C=CC=CN=1)C.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[C:35]([NH:54][C@H:55]([C:59]([O:61][CH2:62][CH:63]([CH2:70][O:71][C:72](=[O:90])[CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH3:89])[CH2:64][CH2:65][CH2:66][C:67]([O:34][CH:17]([CH2:16][O:15][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:12](=[O:14])[CH:13]=[C:4]([C:1]([OH:3])=[O:2])[O:5]2)[CH2:18][O:19][C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[C:22](=[O:33])[CH:23]=[C:24]([C:30]([OH:32])=[O:31])[O:25]2)=[O:68])=[O:60])[CH:56]([CH3:58])[CH3:57])([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 2882CromolynHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 154851735-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoic acid

Product 1

HCID 233875142-[5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoyloxy]-1,3-bis-(2-carboxychromon-5-yloxy)propane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the dibenzyl ester of 1,3-bis-(2-carboxychromon-5-yloxy)propan-2-ol (270 mg, 0.42 mmole), 5-(N-Trityl-L-valyloxymethyl)-6-stearoyloxyhexanoic acid (323 mg, 0.42 mmole) and dimethylaminopyridine (6 mg, 0.05 mmol) in dichloromethane was added DCC (92 mg, 0.45 mmol). After 3 days, the reaction mixture was filtered through Celite and the filtrate was washed with sodium hydrogen carbonate aqueous solution and dried. The product dibenzyl ester of 2-[5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoyloxy]-1,3-bis-(2-carboxychromon-5-yloxy)propane was isolated from silica gel column chromatography. 250 mg.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. washthe filtrate was washed with sodium hydrogen carbonate aqueous solution
  3. customdried

Sources & evidence

ORD record
ord-fd20f28d700a4501bc44215d6057655f
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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