Triethylamine → HCID 57842770, compound

HRID 735623Notes

Reaction equation

HRID 735623 reaction equation
CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.[C:29]([C:32]1[CH:33]=[C:34]([NH:38][CH:39]([C:43]2[CH:48]=[CH:47][C:46]([CH2:49][CH2:50][OH:51])=[C:45]([CH2:52][CH3:53])[CH:44]=2)[C:40](O)=[O:41])[CH:35]=[CH:36][CH:37]=1)(=[O:31])[NH2:30].[CH:54]([S:57][C:58]1[CH:64]=[CH:63][C:61]([NH2:62])=[CH:60][C:59]=1[CH2:65][NH:66][CH3:67])([CH3:56])[CH3:55]>CCOC(C)=O>[NH2:62][C:61]1[CH:63]=[CH:64][C:58]([S:57][CH:54]([CH3:56])[CH3:55])=[C:59]([CH:60]=1)[CH2:65][N:66]([CH3:67])[C:40](=[O:41])[CH:39]([NH:38][C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=1)[C:29]([NH2:30])=[O:31])[C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50][OH:51])=[C:45]([CH2:52][CH3:53])[CH:44]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 57842645HCID 57842645, compoundHCID 57842901HCID 57842901, compound

Product 1

HCID 57842770HCID 57842770, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

EDCI (67 mg, 0.35 mmol), HOAt (80 mg, 0.58 mmol) and triethylamine (0.79 mL, 0.58 mmol) were added to a solution of 46C (100 mg, 0.3 mmol) and 16D (67 mg, 0.3 mmol) and stirred at 50° C. for 4 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried over Na2SO4 and concentrated in vacuo. The crude oil was purified by flash chromatography (0% to 20% MeOH in CH2Cl2) to yield 46D as a yellow solid. MS (ESI) m/z 535.4 (M+H)+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude oil was purified by flash chromatography (0% to 20% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-8b8efddf5b3d4a1686f57dd4a9d6584a
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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