Triethylamine → HCID 178472666, compound

HRID 1266707Notes

Reaction equation

HRID 1266707 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1)[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[C:8]([O:15][CH2:16][CH3:17])[C:7]=1[F:18])[CH3:2].C(N(CC)CC)C.Cl.[NH2:37][OH:38]>C(O)C>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[C:8]([O:15][CH2:16][CH3:17])[C:7]=1[F:18])[NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[NH:27])[NH:37][OH:38])=[CH:22][CH:21]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 70004790HCID 70004790, compound

Product 1

HCID 178472666HCID 178472666, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The (RS)-(4-cyano-phenylamino)-(3,5-diethoxy-2-fluoro-phenyl)-acetic acid ethyl ester (136 mg) described in example 2.2 was dissolved in ethanol. Triethylamine (712 mg) and hydroxylamine hydrochloride (245 mg) were added and the mixture was stirred for 18 h at room temperature. The mixture was concentrated; the residue was dissolved in CH2Cl2 and washed with water. The product was purified by column chromatography (CH2Cl2/MeOH) to give 87 mg of (RS)-(3,5-diethoxy-2-fluoro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid ethyl ester as a colorless foam. MS: 420 ([M+H]+).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. customThe product was purified by column chromatography (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-72c783979d164211809cebe3772daff2
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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