Triethylamine → HCID 20610220, compound

HRID 433813Notes

Reaction equation

HRID 433813 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]1[C:15]([CH2:18][S:19][C:20]2[NH:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[N:21]=2)([CH2:16][OH:17])[O:14][C:13](=[O:29])[C:12]=1[OH:30].Cl.[CH3:32][N:33]([CH2:35][C:36](Cl)=[O:37])[CH3:34].C(N(CC)CC)C>CN(C=O)C.Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]1[C:15]([CH2:16][O:17][C:36](=[O:37])[CH2:35][N:33]([CH3:34])[CH3:32])([CH2:18][S:19][C:20]2[NH:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[O:14][C:13](=[O:29])[C:12]=1[OH:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 18758497HCID 18758497, compound

Product 1

HCID 20610220HCID 20610220, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(1H-benzoimidazol-2-ylsulfanyl)-5-(1H-benzoimidazol-2-ylsulfanylmethyl)-3-hydroxy-5-hydroxymethyl-5H-furan-2-one (220 mg, 0.50 mmol), dimethylaminoacetyl chloride hydrochloride (174 mg, 1.10 mmol) and triethylamine (0.280 mL, 2.00 mmol) in DMF (15 mL) was stirred for 22 h. The reaction mixture was then passed through a plug of SiO2, which was then washed with hexane to remove excess DMF, and subsequently with a 1:1 mixture of EtOAc and MeOH to collect dimethylamino-acetic acid 3-(1H-benzoimidazol-2-ylsulfanyl)-2-(1H-benzoimidazol-2-ylsulfanylmethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-2-ylmethyl ester. Upon evaporation of solvent, the residue was subjected to column chromatography (SiO2:CH2Cl2:MeOH:Acetic Acid, 87:10:3 v/v/v) which yielded an off-white solid which was dissolved in 0.5 M HCl and lyophilized (73 mg, 26%, GLI-1007817b). 1H NMR (D2O, 300.16 MHz) δ: 7.20-7.38 (m, 8H), 4.67 (q, J=12.0 Hz, 2H), 3.9104.18 (m, 4H), 2.86-2.96 (m, 6H).). 13C NMR (D2O, 75.04 MHz) δ: 167.4, 165.4, 155.7, 147.2, 145.3, 131.5, 130.9, 126.2, 126.1, 113.1, 112.7, 102.0, 85.2, 65.8, 56.6, 43.7, 36.4. MS (ESI-Pos) m/z: 526.2 (M+H+).

Workup

  1. washwas then washed with hexane
  2. customto remove excess DMF
  3. additionsubsequently with a 1:1 mixture of EtOAc and MeOH
  4. customto collect dimethylamino-acetic acid 3-(1H-benzoimidazol-2-ylsulfanyl)-2-(1H-benzoimidazol-2-ylsulfanylmethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-2-ylmethyl ester
  5. customUpon evaporation of solvent
  6. customyielded an off-white solid which

Sources & evidence

ORD record
ord-706df80937af45dc99ac9426522d801a
Source dataset
uspto-grants-2003_12
Patent number
US06667330B2

Reaction notes

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