Methanol → HCID 67154657, compound

HRID 2172100Notes

Reaction equation

HRID 2172100 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-726c3fb486474533b02927e189d2e2f1
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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