Triethylamine → HCID 84426875, compound

HRID 926232Notes

Reaction equation

HRID 926232 reaction equation
[S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:18][O:19][CH:20]([O:23][CH3:24])[CH2:21][NH2:22].CCN(CC)CC>C(Cl)Cl>[CH3:18][O:19][CH:20]([O:23][CH3:24])[CH2:21][NH:22][S:1]([C:4]1[C:16]2[C:8](=[C:9]([N:10]([CH3:12])[CH3:11])[CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 84426875HCID 84426875, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of dansyl chloride (270 mg, 1.00 mmol) in CH2Cl2 (10 mL) was added aminoacetaldehyde dimethyl acetal (130 μL, 1.2 mmol) and Et3N (170 μL, 1.2 mmol); the solution was allowed to stir for 1 h at 25° C. The reaction mixture was then evaporated to dryness under reduced pressure and the material left was purified by silica gel chromatography using a gradient of MeOH (0→1%) in CH2Cl2 as the eluent. Fractions containing the product were collected and evaporated to dryness under low pressure affording 11 (318 mg, 940 μmol) as a solid in a yield of 94%. 1H NMR (300 MHz, DMSO-d6): δ 8.45 (dt, J=8.5, 1.1 Hz, 1H), 8.29 (dt, J=8.8, 0.9 Hz, 1H), 8.16 (t, J=5.5 Hz, 1H), 8.10 (dd, J=7.3, 1.1 Hz, 1H), 7.61 (t, J=8.5 Hz, 1H), 7.58 (t, J=8.5 Hz, 1H), 7.25 (dd, J=7.6, 0.7 Hz, 1H), 4.11 (t, J=5.5 Hz, 1H), 3.06 (s, 6H), 2.89 (t, J=5.5 Hz, 2H), 2.81 (s, 6H). 13C NMR (75 MHz, DMSO-d6): δ 151.2, 136.2, 129.3, 128.9, 127.9, 127.7, 123.5, 119.1, 115.0, 102.4, 53.3, 44.9, 43.9. +ESI-HRMS: Calcd for C16H22N2O4S [M+H]+ 339.1373. found 339.1374.

Workup

  1. customThe reaction mixture was then evaporated to dryness under reduced pressure
  2. waitthe material left
  3. customwas purified by silica gel chromatography
  4. additionFractions containing the product
  5. customwere collected
  6. customevaporated to dryness under low pressure

Sources & evidence

ORD record
ord-087156e4a0d74fcfb71a0720e79a05e2
Source dataset
uspto-grants-2016_03
Patent number
US09284343B2

Reaction notes

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