Triethylamine → HCID 66838782, compound

HRID 1889220Notes

Reaction equation

HRID 1889220 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[O:10])=[CH:4][CH:3]=1.CCN(CC)CC.[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](Cl)=[O:37]>C(Cl)Cl>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([C:12]([NH:11][C:9](=[O:10])[NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:36](=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][Br:31])=[CH:7][CH:6]=2)=[O:23])=[CH:18][CH:17]=1)([CH3:20])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 5211735-Bromovaleryl chlorideHCID 66838618HCID 66838618, compound

Product 1

HCID 66838782HCID 66838782, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The deprotected amine (368 mg, 0.70 mmol) was stirred in dry CH2Cl2 (10 mL) under N2 atmosphere and NEt3 (98 μL, 0.70 mmol) was added to give a clear brown solution. 5-Bromovaleryl chloride (140 μL, 1.05 mmol, 1.5. equiv.) was added followed by triethylamine (98 μL, 0.70 mmol). The reaction mixture was stirred at rt for 16 h then diluted with CH2Cl2 (1×20 mL) and washed with 1 M aqueous hydrochloric acid (1×20 mL), 1 M aqueous sodium hydroxide (1×20 mL) and saturated brine (1×20 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give a crude yellow chalky solid which was purified by column chromatography on silica (50% ethyl acetate/petroleum ether) to give 29 (153 mg, 48%) as a yellow solid.

Workup

  1. customto give a clear brown solution
  2. washwashed with 1 M aqueous hydrochloric acid (1×20 mL), 1 M aqueous sodium hydroxide (1×20 mL) and saturated brine (1×20 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a crude yellow chalky solid which
  6. customwas purified by column chromatography on silica (50% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-6c100e5054e340769176fef74ef0b22d
Source dataset
uspto-grants-2013_08
Patent number
US08501991B2

Reaction notes

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