Water → Benzyl 4-(4-carboxymethylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

HRID 1176607Notes

Reaction equation

HRID 1176607 reaction equation
[N+](=CC(C1C=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH:13]2[O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]3[O:38][CH2:37][CH2:36][N:35]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:34]=3[CH:44]=2)=[CH:8][CH:7]=1)=O)=[N-].[OH2:45].[O:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1>C(N(CC)CC)C.FC(F)(F)C([O-])=O.[Ag+]>[C:50]([CH2:49][C:48]1[CH:7]=[CH:8][C:9]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])[CH2:14][CH:13]2[O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]3[O:38][CH2:37][CH2:36][N:35]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:34]=3[CH:44]=2)=[CH:10][CH:47]=1)([OH:46])=[O:45]

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 86610026benzyl 4-[4-(2-diazoacetyl)phenyl]-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Product 1

HCID 68501339Benzyl 4-(4-carboxymethylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
-10 °C

Procedure

The solution of 0.228 g of benzyl 4-[4-(2-diazoacetyl)phenyl]-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate in 3.5 ml of tetrahydrofuran is cooled to −15° C., protected from light and admixed with a solution of 0.025 g of silver trifluoroacetate in 0.153 ml of triethylamine, then 0.4 ml of water. The reaction mixture is stirred at −10° C. for 30 minutes, then at 15° C. for 24 hours, and concentrated by evaporation. The residue is dissolved in 10 ml of 0.1N NaOH and washed with 50 ml of tert-butyl methyl ether. The aqueous phase is acidified to pH 1.0 with 2N HCl and washed three times with 30 ml of tert-butyl methyl ether. The combined organic phases are dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue. Rt=4.72.

Workup

  1. waitat 15° C. for 24 hours
  2. concentrationconcentrated by evaporation
  3. dissolutionThe residue is dissolved in 10 ml of 0.1N NaOH
  4. washwashed with 50 ml of tert-butyl methyl ether
  5. washwashed three times with 30 ml of tert-butyl methyl ether
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b85a50af705a450b98c2efa5612ab103
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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