Diisopropylethylamine → HCID 11362797, compound

HRID 1869266Notes

Reaction equation

HRID 1869266 reaction equation
[NH2:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].Cl.CCN(C(C)C)C(C)C.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][C:31]2[S:35][C:34]([S:36](Cl)(=[O:38])=[O:37])=[CH:33][CH:32]=2)=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl.CN(C=O)C>[C:6]([O:5][C:3](=[O:4])[CH2:2][NH:1][S:36]([C:34]1[S:35][C:31]([CH2:30][NH:29][C:27]([C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=2)=[O:28])=[CH:32][CH:33]=1)(=[O:38])=[O:37])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 27357135-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chloride

Product 1

HCID 11362797HCID 11362797, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

H-Gly-OtBu.HCl (263 mg, 1.57 mmol) is dissolved in 20 ml CH2Cl2. pH is adjusted to 9 using i-Pr2NEt as a base (537 μl, 3.14 mmol). To this solution is added dropwise 1b (500 mg, 1.43 mmol) in 10 ml DMF. The reaction is stirred overnight. 30 ml of CH2Cl2 are added and the organic phase washed with HCl (0.1N) and sat. NaCl sol. Drying over MgSO4 and evaporating the solvent to dryness affords 1c (400 mg, 63%) as a white solid. mp °C., 1H NMR (d6-DMSO) δ 9.34 (t, J=6.40 Hz, 1H), 8.25 (t, J=6.40 Hz, 1H), 7.89 (d, J=8.67 Hz, 2H), 7.56 (d, J=8.67 Hz, 2H), 7.41 (d, J=3.77 Hz, 1H), 7.05 (d, J=3.7 Hz, 1H), 4.62 (d, J=6.40 Hz, 2H), 3.59 (d, J=6.40 Hz, 2H), 1.3 (s, 9H).

Workup

  1. washthe organic phase washed with HCl (0.1N) and sat. NaCl sol.
  2. dry with materialDrying over MgSO4
  3. customevaporating the solvent to dryness

Sources & evidence

ORD record
ord-e0831879cd60448bac8e0121badc80f8
Source dataset
uspto-grants-2009_12
Patent number
US07638538B1

Reaction notes

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