Triethylamine → HCID 57864664, compound

HRID 1917075Notes

Reaction equation

HRID 1917075 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:10][CH2:11][NH2:12])[CH:6]=[CH:7][CH:8]=1.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C(N(CC)CC)C>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:10][CH2:11][NH:12][C:14](=[O:15])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 24697918HCID 24697918, compound

Product 1

HCID 57864664HCID 57864664, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 20 (1.0 g) in EtOAc (50 mL) cooled to ˜0° C. was added benzyl chloroformate (1.1 eq.) and triethylamine (1.2 eq.). The reaction mixture was stirred for 4 hours at r.t. and washed with 1N HCl, and sat. NaHCO3 (2×10 mL). The solvents were removed by evaporation under reduced pressure to give crude title product. Purification by chromatography gave 21 as white solid. Yield: 1.61 g.

Workup

  1. washwashed with 1N HCl, and sat. NaHCO3 (2×10 mL)
  2. customThe solvents were removed by evaporation under reduced pressure
  3. customto give crude title product
  4. customPurification by chromatography

Sources & evidence

ORD record
ord-65105db8eff641d5b6b6273ddff02cc0
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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