Triethylamine → HCID 57864655, compound

HRID 1917077Notes

Reaction equation

HRID 1917077 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7][CH2:8][CH2:9][NH2:10])=[CH:3][CH:2]=1.Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C([O-])([O-])=O.[Cs+].[Cs+].C(N(CC)CC)C>CCOC(C)=O.O>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7][CH2:8][CH2:9][NH:10][C:13](=[O:14])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 10796Cesium carbonateHCID 420617HCID 420617, compound

Product 1

HCID 57864655HCID 57864655, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 24 (1.60 g) in EtOAc (100 mL) was added benzyl chloroformate (2.0 g, 1.2 eq.) and Cs2CO3 (3.2 g, 3 eq.). The reaction mixture was stirred at r.t. for 5 h. Triethylamine (2 mL) was added and the reaction was stirred for 3 h. After addition of H2O (30 mL), the organic phase was separated and washed with 1N HCl (2×30 mL), and sat. NaHCO3 (2×30 mL). The solvent was removed by evaporation under reduced pressure to give product 25 as white solid. Yield: 2.4 g, 79.7%.

Workup

  1. stirringthe reaction was stirred for 3 h
  2. customthe organic phase was separated
  3. washwashed with 1N HCl (2×30 mL), and sat. NaHCO3 (2×30 mL)
  4. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-996d2b892bd4456888228dbefdf3f6ad
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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