Sodium Hydroxide → HCID 21092439, compound

HRID 1348950Notes

Reaction equation

HRID 1348950 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][CH:5]([C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][N:18]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]2)=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)C>[C:26]([O:25][C:23]([NH:22][N:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][C:12]([CH:5]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=3)[CH2:4][C:3]([OH:30])=[O:2])=[CH:13][CH:14]=2)[CH2:19]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69144367HCID 69144367, compound

Product 1

HCID 21092439HCID 21092439, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-[2-(tert-butyloxycarbonylamino)-1,2,3,4-tetrahydro-isoquinolin-7-yl]-3-(pyrid-4-yl)-propionic acid methyl ester {1.46 g, Reference Example 15(b)} in ethanol (100 mL) was treated with sodium hydroxide solution (6 mL, 1N). This mixture was heated at 80° C. for 9 hours and then evaporated. The residue was partitioned between ethyl acetate and water which had been adjusted to pH 6 by addition of dilute hydrochloric acid. the aqueous phase was extracted twice with ethyl acetate and the combined organics were washed with water and then evaporated to give the title compound (0.6 g) which was used without further purification.

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate and water which
  3. additionhad been adjusted to pH 6 by addition of dilute hydrochloric acid
  4. extractionthe aqueous phase was extracted twice with ethyl acetate
  5. washthe combined organics were washed with water
  6. customevaporated

Sources & evidence

ORD record
ord-5c41ac537b4048d28f315c785647cb5b
Source dataset
uspto-grants-2007_05
Patent number
US07211586B2

Reaction notes

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