Sodium Hydroxide → HCID 69102892, compound

HRID 2220421Notes

Reaction equation

HRID 2220421 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:35][C@H:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26]C)=[O:25])=[C:20]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:19]=2)=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]([CH2:35][C@H:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[C:20]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:19]=2)=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69102509HCID 69102509, compound

Product 1

HCID 69102892HCID 69102892, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4′-[3-[(tert-butoxycarbonyl)-[(2R)-2-hydroxy-2-phenylethyl]amino]propyl]-3-(cyclohexyloxy)-4-biphenylcarboxylate (147 mg) in methanol (2.94 ml) was added 1N sodium hydroxide (0.5 ml) and the mixture was stirred at room temperature for 18 hours, at which time the starting material was still remained. The mixture was warmed to 50° C. and stirred for 3 hours, at which time the reaction was complete. After cooling to room temperature, the mixture was quenched by the addition of 1N hydrochloric acid (0.5 ml) and diluted with ethyl acetate (10 ml). The mixture was with water (10 ml×2) and brine (10 ml), and dried over magnesium sulfate. Filtration followed by evaporation gave 4′[3-[(tert-butoxycarbonyl)-[(2R)-2-hydroxy-2-phenylethyl]amino]propyl]-3-(cyclohexyloxy)-4-biphenylcarboxylic acid (141 mg) as a pale yellow solid.

Workup

  1. temperatureThe mixture was warmed to 50° C.
  2. stirringstirred for 3 hours, at which time the reaction
  3. temperatureAfter cooling to room temperature
  4. customthe mixture was quenched by the addition of 1N hydrochloric acid (0.5 ml)
  5. additiondiluted with ethyl acetate (10 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration
  8. customfollowed by evaporation

Sources & evidence

ORD record
ord-d80f9f4c27f44c9b82cbfce0380a93bd
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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