Dimethylformamide → HCID 88142180, compound

HRID 1587593Notes

Reaction equation

HRID 1587593 reaction equation
[CH:1]1([C:6]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:25]([NH:27][C@@H:28]([CH2:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[CH:29]([P:31]([O:35][CH3:36])([O:33][CH3:34])=[O:32])[OH:30])=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:44].O[C:46]1[C:54]2N=NN[C:50]=2[CH:49]=[CH:48][CH:47]=1.C([N:57]([CH2:60]C)CC)C.Cl.CN(C)CCCN=C=NCC.CN(C)[CH:76]=[O:77]>>[C:46]1([CH2:76][O:77][C:60]([NH:57][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][C:6]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:25]([NH:27][C@@H:28]([CH2:37][CH:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)[CH:29]([P:31]([O:33][CH3:34])([O:35][CH3:36])=[O:32])[OH:30])=[O:26])[CH2:21][CH:22]([CH3:23])[CH3:24])=[O:18])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])=[O:44])[CH:54]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10009053HCID 10009053, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 88142180HCID 88142180, compound

Conditions

Temperature
0 °C

Procedure

The title A compound of Example 5 (1.24 g, 3 mmol) was added to a solution of the title C compound (1.27 g, 3 mmol) in dimethylformamide (15 mL) and cooled to 0° C. Hydroxybenzotriazole hydrate 459 mg, 3 mmol), triethylamine (501.9 ml, 3.6 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (575.1 mg, 3 mmol) were added sequentially. After 16 hours at 25° C., pH 4.01 buffer solution was added and the reaction mixture was stirred for 10 minutes. The resulting precipitate was filtered and washed sequentially with pH 4.01 buffer (3×50 mL), water (3×50 mL), saturated aqueous sodium hydrogen carbonate (50 mL) and dried over sodium sulfate yielding 1.6 g of crude material. Purification by flash chromatography afforded 770 mg of slightly impure product and 566.1 mg of pure title D compound, which was characterized by 13MS and 13NMR.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed sequentially with pH 4.01 buffer (3×50 mL), water (3×50 mL), saturated aqueous sodium hydrogen carbonate (50 mL)
  3. dry with materialdried over sodium sulfate yielding 1.6 g of crude material
  4. customPurification by flash chromatography
  5. customafforded 770 mg of slightly impure product and 566.1 mg of pure title D compound, which

Sources & evidence

ORD record
ord-1fc6e0f06c094836ac79d3fdea662cfc
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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