Sodium Carbonate → HCID 78324477, compound

HRID 2201915Notes

Reaction equation

HRID 2201915 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Br[CH2:25][C:26]([O:28]C(C)(C)C)=[O:27].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][O:23][CH2:25][C:26]([OH:28])=[O:27])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 79177tert-Butyl bromoacetateHCID 118558226HCID 118558226, compound

Product 1

HCID 78324477HCID 78324477, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (R)-2-(4′-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)ethanol (80 mg, 0.259 mmol) and tert-butyl 2-bromoacetate (605 mg, 3.10 mmol) in CHCl3 (3 mL) was added 2M Na2CO3 (1.939 mL, 3.88 mmol). The mixture was stirred overnight at 55° C. The aqueous layer was separated, washed with DCM, and neutralized with 2M HCl. The aqueous mixture was then purified by HPLC. LCMS m/z=368.4 [M+H]+.

Workup

  1. customThe aqueous layer was separated
  2. washwashed with DCM
  3. customThe aqueous mixture was then purified by HPLC

Sources & evidence

ORD record
ord-79ad8b2bd98a44c0a6191a769d2134f9
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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