Ethyl Acetate → HCID 69100376, compound

HRID 2114995Notes

Reaction equation

HRID 2114995 reaction equation
C(OCC)(=O)C.C(OC([N:14]1[C:22]2[C:17](=[CH:18][C:19]([NH:23][C:24](=[O:40])[C:25]([N:27]3[CH2:32][CH2:31][CH:30]([CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:29][CH2:28]3)=[O:26])=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)=O)(C)(C)C>Cl>[CH2:33]([CH:30]1[CH2:29][CH2:28][N:27]([C:25](=[O:26])[C:24]([NH:23][C:19]2[CH:18]=[C:17]3[C:22](=[CH:21][CH:20]=2)[NH:14][CH2:15][CH2:16]3)=[O:40])[CH2:32][CH2:31]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 69100544HCID 69100544, compound

Product 1

HCID 69100376HCID 69100376, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 10 ml of 2.5 M hydrochloric acid in ethyl acetate 0.9 g (2.0 mmol) of 5-[2-(4-benzyl-piperidin-1-yl)-2-oxo-acetylamino]-2,3-dihydro-indol-1-carboxylic acid tert-butyl ester is added. The reaction mixture is stirred for 3 hours at 20° C., then concentrated. The product is transformed into base form with 2 M sodium carbonate solution, extracted with chloroform, the organic layer is concentrated and the residue is dried to yield 0.45 g (64.1%) of the title compound. Melting Point: 152° C.

Workup

  1. concentrationconcentrated
  2. extractionextracted with chloroform
  3. concentrationthe organic layer is concentrated
  4. customthe residue is dried

Sources & evidence

ORD record
ord-af02f4bb64b74a11be985b2012c10ef1
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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