Hydrochloric Acid → HCID 68705812, compound

HRID 2261889Notes

Reaction equation

HRID 2261889 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([C:18]1[O:22][C:21]([C:23]2[CH:24]=[C:25]([C:37]([O:39]C)=[O:38])[CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]#[N:36])[CH:28]=2)=[N:20][N:19]=1)([CH3:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.Cl>CO>[C:1]([O:5][C:6]([NH:8][C:9]([C:18]1[O:22][C:21]([C:23]2[CH:24]=[C:25]([C:37]([OH:39])=[O:38])[CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]#[N:36])[CH:28]=2)=[N:20][N:19]=1)([CH3:17])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68707742HCID 68707742, compound

Product 1

HCID 68705812HCID 68705812, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of methyl 5-(5-{(1R)-1-[(tert-butoxycarbonyl)amino]-1-methyl-2-phenylethyl}-1,3,4-oxadiazol-2-yl)-2′-cyanobiphenyl-3-carboxylate from Step A (780 mg, 1.45 mmole) in methanol (20 mL) at rt was added 0.43 mL of 5 N NaOH aq. The reaction was allowed to stir at rt overnight. The solution was poured into water (100 mL) and acidified by adding 1N HCl (10 mL). The resulting mixture was extracted with ethyl acetate (2×100 mL). The combined organics were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated at reduced pressure to give 5-(5-{1-[(tert-butoxycarbonyl)amino]-1-methyl-2-phenylethyl}-1,3,4-oxadiazol-2-yl)-2′-cyanobiphenyl-3-carboxylic acid (Intermediate XVII). 1H NMR (400 MHz, CDCl3) δ 8.77 (br s, 1H), 8.47 (m, 2H), 7.84 (d, J=7.7 Hz, 1H), 7.72 (t, J=7.7 Hz, 1H), 7.65-7.55 (m, 2H), 7.33-7.25 (m, 3H), 7.13-7.05 (2H, m) 5.25 (br s, 1H), 3.61 (d, J=13.5 Hz, 1H), 3.46 (d, J=13.5 Hz, 1H), 1.76 (s, 3H), 1.42 (s, 9H). LCMS [(M)+H]+=525

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  2. washThe combined organics were washed with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-6926d1a48a5d459b8c79bae0b5e83ebc
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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