Methanol → HCID 67154657, compound

HRID 633999Notes

Reaction equation

HRID 633999 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:31][C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[CH:28]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>ClCCl>[ClH:1].[S:31]1[C:27]([CH2:26][O:25][CH:23]2[CH2:22][NH:21][CH2:24]2)=[CH:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 67154560HCID 67154560, compound

Product 1

HCID 67154657HCID 67154657, compoundYield 213.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (322 μL, 1.1 mmol) was added to a solution of 1-benzhydryl-3-(benzo[b]thiophen-2-ylmethoxy)-azetidine (1.04 g, 2.7 mmol) in dichloromethane (17 mL) at room temperature. The reaction mixture was stirred for 2 hours. Methanol (17 mL) was added and the reaction mixture was stirred for an additional 16 hours at room temperature. The reaction mixture was then concentrated to dryness and the residue was triturated in petroleum ether (20 mL) to afford the title compound as a yellow solid (600 mg, 90%).

Workup

  1. stirringthe reaction mixture was stirred for an additional 16 hours at room temperature
  2. concentrationThe reaction mixture was then concentrated to dryness
  3. customthe residue was triturated in petroleum ether (20 mL)

Sources & evidence

ORD record
ord-ff153325f7db4f708df1c41eabb70546
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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