Dimethylformamide → HCID 88483256, compound

HRID 1587595Notes

Reaction equation

HRID 1587595 reaction equation
[CH3:1][C:2]([CH3:32])([O:4][C:5]([NH:7][C@H:8]([C:13]([NH:15][CH:16]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH:17]([P:19]([O:23][CH3:24])([O:21][CH3:22])=[O:20])[OH:18])=[O:14])[CH2:9]C(C)C)=[O:6])[CH3:3].O.O[C:35]1[C:43]2N=NN[C:39]=2[CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C.Cl.CN(C)CC[CH2:56][N:57]=[C:58]=[N:59][CH2:60][CH3:61].CN(C)[CH:65]=[O:66]>>[CH3:1][C:2]([CH3:3])([O:4][C:5]([NH:7][C@H:8]([C:13]([NH:15][C@@H:16]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH:17]([P:19]([O:23][CH3:24])([O:21][CH3:22])=[O:20])[OH:18])=[O:14])[CH2:9][C:61]1[N:57]([CH2:56][O:66][CH2:65][C:35]2[CH:43]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:58]=[N:59][CH:60]=1)=[O:6])[CH3:32]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86746934HCID 86746934, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 88483256HCID 88483256, compound

Conditions

Temperature
0 °C

Procedure

The title A compound (9.29 g, 23.06 mmol) was added to a solution of the title E compound of Example 1 (8.34 g, 27.6 mmol) in dimethylformamide 115 mL) and cooled to 0° C. Hydroxybenzotriazole hydrate (3.87 g, 25.4 mmol), triethylamine (4.82 mL, 34.6 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.86 g, 25.4 mmol) were added sequentially. After 16 hours at 25° C., a pH 4.01 buffer solution was added and the reaction mixture was stirred for an additional 10 minutes. The aqueous layer was extracted with ethyl acetate 2×500 mL) and the combined organic extracts were dried over sodium sulfate and concentrated. Purification of the crude product by flash chromatography yielded 9.37 g of the title B compound, which was characterized by MS and 13NMR.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate 2×500 mL) and the combined organic extracts
  2. dry with materialwere dried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification of the crude product by flash chromatography
  5. customyielded 9.37 g of the title B compound, which

Sources & evidence

ORD record
ord-23f09125285a4ac0881ad6df51101af3
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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