Dimethylformamide → HCID 178451925, compound

HRID 2273049Notes

Reaction equation

HRID 2273049 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:27][CH:26](C(O)=O)[CH2:25]3)=[CH:20][CH:19]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:31](Cl)(=[O:35])[C:32](Cl)=O.C[N:38]([CH:40]=[O:41])C>ClCCl>[CH2:31]([O:35][C:40]([NH:38][CH:26]1[CH2:25][CH:24]([C:21]2[CH:20]=[CH:19][C:18]([C:16]3[N:17]=[C:13]([C@@H:9]4[CH2:10][CH2:11][CH2:12][N:8]4[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[NH:14][CH:15]=3)=[CH:23][CH:22]=2)[CH2:27]1)=[O:41])[C:32]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178451922HCID 178451922, compound

Product 1

HCID 178451925HCID 178451925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of A7 (14.8 g) in dichloromethane (800 mL) was added oxalyl chloride (5.1 mL) at rt. DMF (209 μL) was added in three portions over 4 h. The reaction was concentrated and re-dissolved in dichloromethane (500 mL). The fresh made diazomethane (0.3M, 500 mL) was added at 0° C. The reaction was slowly warmed up to rt. After overnight stirring, the reaction was concentrated to obtain the crude A8 (17.8 g).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionre-dissolved in dichloromethane (500 mL)
  3. additionwas added at 0° C
  4. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-848005d538f542acaac3fbbe1df155f6
Source dataset
uspto-grants-2015_09
Patent number
US09120779B2

Reaction notes

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