Hydrochloric Acid → 2-{4-[2-Tert-butoxycarbonylamino-3-(4-fluorophenyl)-propionyl]-3-methoxymethyl-piperazine-1-yl}-3-naphthalen-2-yl-propionic acid

HRID 720202Notes

Reaction equation

HRID 720202 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:46])[CH:6]([N:18]1[CH2:23][CH2:22][N:21]([C:24](=[O:42])[CH:25]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH:20]([CH2:43][O:44][CH3:45])[CH2:19]1)[CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1.Cl>C1COCC1.O>[C:38]([O:37][C:35]([NH:34][CH:25]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[C:24]([N:21]1[CH2:22][CH2:23][N:18]([CH:6]([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[C:5]([OH:46])=[O:4])[CH2:19][CH:20]1[CH2:43][O:44][CH3:45])=[O:42])=[O:36])([CH3:41])([CH3:39])[CH3:40]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69587795HCID 69587795, compound

Product 1

HCID 219016992-{4-[2-Tert-butoxycarbonylamino-3-(4-fluorophenyl)-propionyl]-3-methoxymethyl-piperazine-1-yl}-3-naphthalen-2-yl-propionic acidYield 100%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

LiOH (0.71 g, 29.7 mmol) is added to the cold solution of 2-{4-[2-tert-butoxycarbonylamino-3-(4-fluorophenyl)-propionyl]-3-methoxymethyl-piperazine-1-yl}-3-naphthalen-2-yl-propionic acid methyl ester, 63, (3.6 g, 5.9 mmol) in THF/H2O (2/1, 60 mL). The reaction mixture is stirred for overnight. The reaction mixture is cooled in ice bath and pH is adjusted to 3 with 1M HCl. The aqueous layer is extracted with EtOAc (3×100 mL) and dried over Na2SO4. The solution is concentrated in vacuo to afford 3.7 g 100% yield) of the desired product.

Workup

  1. temperatureThe reaction mixture is cooled in ice bath
  2. extractionThe aqueous layer is extracted with EtOAc (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-1f0782611a944d578ecadfcddb8422e9
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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