Dichloromethane → HCID 11992667, compound

HRID 2241049Notes

Reaction equation

HRID 2241049 reaction equation
[C:1]1([C:7](=[C:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16](O)=[O:17])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.C(Cl)(=O)C(Cl)=O.[NH4+:38].[OH-]>O>[C:1]1([C:7](=[C:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([NH2:38])=[O:17])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 11992666HCID 11992666, compound

Product 1

HCID 11992667HCID 11992667, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 34 (100 mg, 0.26 mmol) and CH2Cl2 (mL) was added oxalyl chloride (90 uL, 1.06 mmol) and the mixture was stirred at RT for 2 h. To this solution 10 mL of NH4OH (30% aqueous) was slowly introduced and stirred for 6 h. The mixture was poured into H2O (100 mL) and then extracted with EtOAc (2×100 mL). The organic layer was worked-out to give the crude product, which upon purification gave 11 mg (11%) of the desired product 35 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.48 (br s, 1H), 7.35 (br s, 1H), 7.27 (app. J=7.6 Hz, 2H), 7.16 (d, J=7.6 Hz, 1H), 7.12 (d, J=7.2 Hz, 2H), 7.06 (d, J=8.8 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 4.36 (s, 2H), 1.91 (s, 2H), 1.87 (s, 2H), 1.25 (s, 2H), 0.88 (s, 6H), 0.87 (s, 6H). LCMS (ESI): m/z 378 (M+H)+.

Workup

  1. stirringstirred for 6 h
  2. extractionextracted with EtOAc (2×100 mL)
  3. customto give the crude product, which
  4. customupon purification

Sources & evidence

ORD record
ord-c49de91f780c476d8b000941af609054
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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