Triethylamine → HCID 69427789, compound

HRID 1375925Notes

Reaction equation

HRID 1375925 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:29][C:30](=[O:32])[CH3:31])([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]=[N:27][OH:28])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].[O-]Cl.[Na+].CCN(CC)CC.[CH:43]#[C:44][CH2:45][CH2:46][CH3:47]>C(Cl)Cl.O>[C:9]([O:8][CH2:7][C:6]([NH:29][C:30](=[O:32])[CH3:31])([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:43]=[C:44]([CH2:45][CH2:46][CH3:47])[O:28][N:27]=3)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 123091-PentyneHCID 23665760Sodium HypochloriteHCID 86591346HCID 86591346, compound

Product 1

HCID 69427789HCID 69427789, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of acetic acid 2-acetoxymethyl-2-acetylamino-4-[4′-(hydroxyimino-methyl)biphenyl-4-yl]butyl ester (0.2 mmol), NaOCl (2 mmol), Et3N (3 mmol) and pentyne (40 mmol) in DCM (4 mL) and H2O (1 mL) is stirred at room temperature for 12 h. It is diluted with DCM (5 mL) and H2O (10 mL) and the organic phase is washed with brine and dried over Na2SO4. After concentrating, the crude product is purified by column chromatography using EtOAc/hexane (1/1) to give the desired product as a white solid. MS: (ES+): 507.2 (M+1)+.

Workup

  1. washthe organic phase is washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationAfter concentrating
  4. customthe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-70076fd405154a5e932318415691a3d2
Source dataset
uspto-grants-2007_01
Patent number
US07169817B2

Reaction notes

Loading…