Triethylamine → HCID 57589793, compound

HRID 1783420Notes

Reaction equation

HRID 1783420 reaction equation
[C:1]([O:5][C:6]([N:8]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:9]1[CH:14]=[C:13]([CH2:15][C@H:16]2[C:19](=[O:20])[NH:18][C@@H:17]2[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N([CH2:43][CH3:44])CC)C.[N-:45]=[C:46]=[O:47]>C1COCC1>[C:1]([O:5][C:6]([N:8]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:9]1[CH:14]=[C:13]([CH2:15][C@H:16]2[C:19](=[O:20])[N:18]([C:46](=[O:47])[NH:45][C:44]3[CH:43]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C@@H:17]2[C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 105034IsocyanateHCID 57589818HCID 57589818, compound

Product 1

HCID 57589793HCID 57589793, compoundYield 169.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Deprotected lactam 19 (72 mg, 0.14 mmol) was dissolved in 4 mL dry THF at room temperature. Triethylamine (71 mg, 5 equiv.) was added, then 42 mg (2.5 equiv.) of the isocyanate. The reaction was stirred overnight under argon and concentrated in vacuo. The residue was purified by column chromatography eluting with methylene chloride to yield 20 (75 mg, 85%). MS: 631.3. [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography
  3. washeluting with methylene chloride

Sources & evidence

ORD record
ord-09f34667e2ad4d39845b49384f16c557
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

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