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 8534

Reaction equation

HRID 8534 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-ac312bfa6c2142b1b46f1ac6eceb4ca3
Source dataset
uspto-grants-2006_08
Patent number
US07087759B2

Linked notes

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