Triethylamine → HCID 137195807, compound

HRID 2408266Notes

Reaction equation

HRID 2408266 reaction equation
[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:32])[C:10]2[N:11]=[CH:12][N:13]([C@@H:16]3[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C@H:18](O)[CH2:17]3)[C:14]=2[N:15]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].CCN(CC)CC.CS(Cl)(=O)=O.[N-:45]=[N+:46]=[N-:47].[Na+]>ClCCl.CN(C)C1C=CN=CC=1.CCOC(C)=O.O>[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:32])[C:10]2[N:11]=[CH:12][N:13]([C@@H:16]3[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:31])[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C@H:18]([N:45]=[N+:46]=[N-:47])[CH2:17]3)[C:14]=2[N:15]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 136331515HCID 136331515, compound

Product 1

HCID 137195807HCID 137195807, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 52 (290 mg 0.65 mmol) in dichloromethane (30 mL) were added 4-dimethylaminopyridine (12 mg, 0.065 mmol) and Et3N (0.45 mL), followed by methanesulfonylchloride dropwise (0.121 mL, 1.30 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 40 min under argon then hydrolyzed with water (20 mL). The organic layer was separated and evaporated. The residual oil was diluted in anhydrous DMF (20 mL). To the solution was added sodium azide (410 mg, 6.5 mmol) and the mixture was heated at 120° C. for 2 h under argon. The reaction was cooled to room temperature, diluted with AcOEt and washed with water. The organic layer was evaporated and the residue was then purified by column chromatography on silica gel column eluting with CH2Cl2-MeOH (9:1) to give 55 (200 mg, 65%) as a white solid. IR 2104 cm−1 (N3); 1H NMR (DMSO-d6) δ 1.08-1.12 (m, 6H, 2×CH3), 2.50-2.79 (m, 2H, H-2′, isobutyryl CH), 2.91-3.01 (m, 1H, H-2′), 4.18-4.23 (m, 1H, H-4′), 4.42-4.56 (m, 2H, H-5′, H-5″), 4.83-4.89 (m, 1H, H-3′), 6.21 (t, 1H, J=5.4 Hz, H-1′), 7.45-7.50 (m, 2H benzoyl), 7.62-7.66 (m, 1H benzoyl), 7.85-7.88 (m, 2H benzoyl), 8.20 (s, 1H, H-8), 11.53 (br s, NH), 11.91 (br s, NH).

Workup

  1. customThe organic layer was separated
  2. customevaporated
  3. additionThe residual oil was diluted in anhydrous DMF (20 mL)
  4. temperaturethe mixture was heated at 120° C. for 2 h under argon
  5. temperatureThe reaction was cooled to room temperature
  6. washwashed with water
  7. customThe organic layer was evaporated
  8. customthe residue was then purified by column chromatography on silica gel column
  9. washeluting with CH2Cl2-MeOH (9:1)

Sources & evidence

ORD record
ord-a6f4e3b35c6e4931b026d0e50590588a
Source dataset
uspto-grants-2014_08
Patent number
US08815829B2

Reaction notes

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