Dimethylformamide → HCID 22103556, compound

HRID 1457189Notes

Reaction equation

HRID 1457189 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([N:8]([CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[C:19]([CH2:29][C:30](O)=[O:31])=[CH:20][C:21]([C:24]3[O:25][CH:26]=[CH:27][N:28]=3)=[CH:22][CH:23]=2)(=[O:11])=[O:10])[O:4][N:3]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[C:50]([NH2:54])([CH3:53])([CH3:52])[CH3:51]>C(Cl)Cl.CCOC(C)=O>[CH3:51][C:50]([NH:54][C:30](=[O:31])[CH2:29][C:19]1[C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:9]([N:8]([C:5]2[O:4][N:3]=[C:2]([CH3:1])[C:6]=2[CH3:7])[CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])(=[O:11])=[O:10])=[CH:23][CH:22]=[C:21]([C:24]2[O:25][CH:26]=[CH:27][N:28]=2)[CH:20]=1)([CH3:53])[CH3:52]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6385Tert-ButylamineHCID 65578Oxalyl chlorideHCID 22103717HCID 22103717, compound

Product 1

HCID 22103556HCID 22103556, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To the title compound of Step (C) (85 mg, 0.16 mmol) and 0.004 ml DMF in 1.6 ml CH2Cl2, oxalyl chloride (2M in CH2Cl2, 0.20 ml, 0.40 mmol) was added. The mixture was stirred at room temperature for 0.5 hr and concentrated. To the residue, 2 ml CH2Cl2 and tert-butylamine (t-BuNH2, 69 mg, 0.94 mmol) were added. The reaction was stirred at room temperature overnight, diluted with EtOAc, washed with H2O and brine, dried and concentrated. The residue was chromatographed on silica gel using 1:2 hexane/EtOAc to afford the title compound of this step (45 mg, 48%) as a colorless gum.

Workup

  1. concentrationconcentrated
  2. stirringThe reaction was stirred at room temperature overnight
  3. washwashed with H2O and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using 1:2 hexane/EtOAc

Sources & evidence

ORD record
ord-d65ce9427fa14454aa47004a29a8a6e2
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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