Triethylamine → HCID 66953038, compound

HRID 1593478Notes

Reaction equation

HRID 1593478 reaction equation
N[C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@@H:3]1[C:15]([O:17][CH3:18])=[O:16].C(N([CH2:24][CH3:25])CC)C>ClCCl>[CH2:11]([O:10][C:8]([C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[C:15]([O:17][CH3:18])=[O:16])=[O:9])[C:25]1[CH:24]=[CH:4][CH:3]=[CH:2][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 10934154HCID 10934154, compound

Product 1

HCID 66953038HCID 66953038, compoundYield 184.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 260B (0.75 g, 2.90 mmol) in dichloromethane (30 mL) at 0° C. was treated with triethylamine (0.35 g, 3.48 mmol) and N-(benzyloxycarbonyoxy)succinimide (0.72 g, 2.90 mmol). The reaction mixture was allowed to warm to room temperature and was stirred for 16 hours. The reaction mixture was diluted with dichloromethane, washed with 10% citric acid (2×50 mL), then saturated NaHCO3 (2×50 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give 1.01 g (yield: 89%) of Compound 260C as an oil. It was used in the next step without further purification.

Workup

  1. washwashed with 10% citric acid (2×50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5f3f3e728544f389ac552fb4e59a3bb
Source dataset
uspto-grants-2007_11
Patent number
US07297695B2

Reaction notes

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