Triethylamine → HCID 86662381, compound

HRID 578684Notes

Reaction equation

HRID 578684 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].C(N([CH2:27][CH3:28])CC)C.[C:29]1(C)[C:30]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:32]=C[CH:34]=1>ClCCl.O>[C:1]([O:5][C:6]([NH:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[CH2:9][CH2:10][O:11][S:35]([C:30]1[CH:31]=[CH:32][C:27]([CH3:28])=[CH:34][CH:29]=1)(=[O:37])=[O:36])=[O:21])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 19104047HCID 19104047, compound

Product 1

HCID 86662381HCID 86662381, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

2 g (6.75 mmol) [3-Hydroxy-1-(3-nitro-phenyl)-propyl]-carbamic acid tert-butyl ester were dissolved in 10 ml dichloromethane and 1.4 ml (20.1 mmol) triethylamine. Under ice-cooling, 1.54 g (8.10 mmol) toluene sulfonic acid chloride in 5 ml dichloromethane were added and the mixture was stirred 30 min at 0° C. and 18 h at room temperature. The reaction mixture was diluted with 10 ml water and 30 ml dichloromethane, the organic layer was separated and washed with water, dried over Na2SO4 and evaporated to dryness. The crude product was used without further purification. 3.05 g, Rt.=3.35 min (method C), LCMS: 351 (M-boc+H).

Workup

  1. temperatureUnder ice-cooling
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude product was used without further purification
  7. custom=3.35 min (method C), LCMS

Sources & evidence

ORD record
ord-4f2d42008b0b432e9e04d7ec36705a3e
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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