Ethyl trifluoromethanesulphonate → HCID 86750985, compound

HRID 1684053Notes

Reaction equation

HRID 1684053 reaction equation
[C:1]([N:4]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)[C:5]([O:7][CH2:8][CH2:9][O:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([CH:19]2[CH2:23][S:22][CH:21]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=3)[S:20]2)=[CH:13][C:12]=1[O:36][CH3:37])=[O:6])(=[O:3])[CH3:2].[CH:45](N(C(C)C)CC)(C)[CH3:46].[O:54](CC)[S:55]([C:58]([F:61])([F:60])[F:59])(=[O:57])=[O:56]>ClCCl>[O-:57][S:55]([C:58]([F:61])([F:60])[F:59])(=[O:56])=[O:54].[C:1]([N:4]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N+:40]=1[CH2:45][CH3:46])[C:5]([O:7][CH2:8][CH2:9][O:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([C@H:19]2[CH2:23][S:22][C@H:21]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=3)[S:20]2)=[CH:13][C:12]=1[O:36][CH3:37])=[O:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 67924Ethyl trifluoromethanesulphonateHCID 81531DiisopropylethylamineHCID 19041813HCID 19041813, compound

Product 1

HCID 86750985HCID 86750985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[-N-acetyl[{2,6-dimethoxy-4-(3-(3,4,5-trimethoxyphenyl)-2,4-dithiolanyl)phenoxy}ethoxycarbonyl]aminomethyl]pyridine (32) (FIG. 26) (0.049 g, 0.076 mmole), diisopropylethylamine (8 μl, 0.076 mmole) and 5 ml anhydrous dichloromethane were cooled to 0° C. under a nitrogen atmosphere. Ethyl triflate (10 μl, 0.076 mmole) was added. The reaction was allowed to warm to room temperature and was stirred for 12 hours. The solvent was removed in vacuo and the remaining residue redissolved in 0.5 ml acetone. The acetone solution was purified by flash column chromatography using 100% ethyl acetate-10/1CHCl3MeOH-4/1CHCl3 /MeOH as eluent. The product was isolated as a 1.6/1.0 trans/cis mixture of diastereomers as a white foam (0.047 g. 75%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe remaining residue redissolved in 0.5 ml acetone
  3. customThe acetone solution was purified by flash column chromatography
  4. customThe product was isolated as a 1.6/1.0 trans/cis mixture of diastereomers as a white foam (0.047 g. 75%)

Sources & evidence

ORD record
ord-e7e0e4c083214fe9b081b0dd61eef770
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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