Acetic acid 2-[1-{2-[2-acetylamino-3-(hydroxyphenyl)propionyl-amino]-3-(4-fluorophenyl)propionyl}-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)-piperazin-2-yl]ethyl ester → 2-[4-[2-[2-Acetylamino-3-(4-hydroxyphenyl)propionylamino]-3-(4-fluorophenyl)propionyl]-3-(2-hydroxyethyl)piperazin-1-yl]-n-methyl-3-naphthalene-2-yl-propionamide

HRID 1072633

Reaction equation

HRID 1072633 reaction equation
[C:1]([NH:4][CH:5]([CH2:48][C:49]1[CH:54]=[CH:53]C=[CH:51][C:50]=1O)[C:6]([NH:8][CH:9]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:30](=[O:33])[NH:31][CH3:32])[CH2:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[CH2:14][CH:13]1[CH2:34][CH2:35][O:36]C(=O)C)=[O:11])=[O:7])(=[O:3])[CH3:2].[O:56]([CH3:58])[Na]>CO>[C:1]([NH:4][CH:5]([CH2:48][C:49]1[CH:54]=[CH:53][C:58]([OH:56])=[CH:51][CH:50]=1)[C:6]([NH:8][CH:9]([CH2:40][C:41]1[CH:42]=[CH:43][C:44]([F:47])=[CH:45][CH:46]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH:18]([CH2:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[C:30]([NH:31][CH3:32])=[O:33])[CH2:14][CH:13]1[CH2:34][CH2:35][OH:36])=[O:11])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 69629098Acetic acid 2-[1-{2-[2-acetylamino-3-(hydroxyphenyl)propionyl-amino]-3-(4-fluorophenyl)propionyl}-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)-piperazin-2-yl]ethyl esterHCID 178418582HCID 178418582, compound

Product 1

HCID 220156832-[4-[2-[2-Acetylamino-3-(4-hydroxyphenyl)propionylamino]-3-(4-fluorophenyl)propionyl]-3-(2-hydroxyethyl)piperazin-1-yl]-n-methyl-3-naphthalene-2-yl-propionamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution acetic acid 2-[1-{2-[2-acetylamino-3-(hydroxyphenyl)-propionylamino]-3-(4-fluorophenyl)propionyl}-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)-piperazin-2-yl]ethyl ester, 65, (7.5 g, 10 mmol) in methanol (50 mL) is added freshly prepared NaOCH3 (0.55 g, 10.1 mmol) and the solution stirred overnight. The solution is concentrated in vacuo, the resulting residue partitioned between dichloromethane and water, the organic layer is dried and concentrated in vacuo to afford the desired product.

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. customthe resulting residue partitioned between dichloromethane and water
  3. customthe organic layer is dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbb9ed36f3664cf4ace2b4c4adbacd65
Source dataset
uspto-grants-2005_06
Patent number
US06911447B2

Linked notes

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