Ethanol → HCID 67154438, compound

HRID 2172044Notes

Reaction equation

HRID 2172044 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][C:27]2[S:28][CH:29]=[C:30]([CH3:32])[CH:31]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[CH3:32][C:30]1[CH:31]=[C:27]([CH2:26][O:25][CH:23]2[CH2:22][NH:21][CH2:24]2)[S:28][CH:29]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 67154647HCID 67154647, compound

Product 1

HCID 67154438HCID 67154438, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (50.0 μL, 0.4 mmol) was added to a solution of 1-benzhydryl-3-(4-methylthiophen-2-ylmethoxy)-azetidine (150.0 mg, 0.4 mmol) in dichloromethane (4.5 mL) at 0° C. The reaction mixture was stirred 3 hours, then 30 minutes at room temperature. Ethanol (6 mL) was added and the reaction mixture was stirred at 35° C. for an additional 4 hours. After concentration to dryness, the crude was triturated in pentane (2×10 mL) to give a yellow solid (94.0 mg, quantitative) which was used in the next step without further purification.

Workup

  1. custom30 minutes
  2. customat room temperature
  3. stirringthe reaction mixture was stirred at 35° C. for an additional 4 hours
  4. concentrationAfter concentration to dryness
  5. customthe crude was triturated in pentane (2×10 mL)
  6. customto give a yellow solid (94.0 mg, quantitative) which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-39a70d6dc8514efb8e35b252e7a4c10e
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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