Water → 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

HRID 8533

Reaction equation

HRID 8533 reaction equation
[NH2:1][CH:2]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:23](=[O:26])[NH:24][CH3:25])[CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)[CH2:7][CH:6]1[CH2:27][CH2:28][O:29][C:30](=[O:32])[CH3:31])=[O:4].[OH:41][C:42]1[C:50]2N=NN[C:46]=2[CH:45]=[CH:44][CH:43]=1.C[N:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.[CH3:58]N(C)CCCN=C=NCC.[OH2:69]>CN(C=O)C>[C:53]([NH:52][CH:57]([CH2:58][C:50]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[OH:41])[C:56]([NH:1][CH:2]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:23](=[O:26])[NH:24][CH3:25])[CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)[CH2:7][CH:6]1[CH2:27][CH2:28][O:29][C:30](=[O:32])[CH3:31])=[O:4])=[O:55])(=[O:69])[CH3:54]

Participants

7

Reactant 5

HCID 962WaterHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69630273Acetic acid 2-{1-[2-amino-3-(4-fluorophenyl)propionyl]-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)piperazin-2-yl}-ethyl esterHCID 178418300HCID 178418300, compound

Product 1

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 ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of acetic acid 2-{1-[2-amino-3-(4-fluorophenyl)propionyl]-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)piperazin-2-yl}-ethyl ester, 64, (54.9 g, 100 mmol), hydroxybenzotriazole (16.2 g, 120 mmol), and N-methylmorpholine (132 mL, 120 mmol) in DMF (150 mL) is cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (24.9 g, 130 mmol) is slowly added. The resulting mixture is stirred for 2 hours at 0° C. then allowed to warm and stir at room temperature another 2 hours. The reaction solution is diluted with water and the resulting solid is collected by filtration, re-dissolved in EtOAc and extracted with water, dried and concentrated in vacuo to afford a residue which purified over silica gel.

Workup

  1. temperatureto warm
  2. stirringstir at room temperature another 2 hours
  3. filtrationthe resulting solid is collected by filtration
  4. dissolutionre-dissolved in EtOAc
  5. extractionextracted with water
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customto afford a residue which
  9. custompurified over silica gel

Sources & evidence

ORD record
ord-dd4587f83f314674afb5cfab26dbd8f9
Source dataset
uspto-grants-2006_08
Patent number
US07087759B2

Linked notes

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