Triethylamine → HCID 86601066, compound

HRID 2215257Notes

Reaction equation

HRID 2215257 reaction equation
[CH2:1]([O:3][CH:4]([O:14][CH2:15][CH3:16])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C(N(CC)CC)C.Cl[CH2:25][CH2:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH2:7]([N:6]([CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:14][CH2:15][CH3:16])[S:27]([CH:26]=[CH2:25])(=[O:29])=[O:28])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 521961(Benzylamino)acetaldehyde diethyl acetal

Product 1

HCID 86601066HCID 86601066, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzylamino-acetaldehyde diethyl acetal (14.6 ml, 61.3 mmol) and triethylamine (19.0 ml, 122.0 mmol) in dichloromethane (200 ml) at 0° C. under argon was added 2-chloro-1-ethanesulfonyl chloride (10.0 g, 61.3 mmol). After stirring at rt for 3 h, the reaction mixture was quenched with water (300 ml), extracted with dichloromethane (200 ml×2), washed with brine (150 ml), dried over MgSO4, filtered, and concentrated in vacuo to give the title compound which was used in next step without further purification; 1H NMR (CDCl3): 1.23 (t, 6H), 3.22(d, 2H), 353 (m, 2H), 3.72 (m, 2H), 4.52 (s, 12H), 4.63 (t, 1H), 5.88 (d, 1H), 6.23 (d, 1H), 6.50–6.43 (m, 1H), 7.35 (m, 5H); LCMS: 268 (MH+−46).

Workup

  1. customthe reaction mixture was quenched with water (300 ml)
  2. extractionextracted with dichloromethane (200 ml×2)
  3. washwashed with brine (150 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf55f1f66bb3491695ae92534b2f85cf
Source dataset
uspto-grants-2006_09
Patent number
US07109233B2

Reaction notes

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