Lithium hydroxide, monohydrate → HCID 68705918, compound

HRID 2261888Notes

Reaction equation

HRID 2261888 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]([CH:31]=[C:32]([C:34]3([C:39]#[N:40])[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH:33]=2)[C:26]([O:28]CC)=[O:27])=[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].O[Li].O>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@:9]([C:18]1[O:22][C:21]([C:23]2[CH:24]=[C:25]([CH:31]=[C:32]([C:34]3([C:39]#[N:40])[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH:33]=2)[C:26]([OH:28])=[O:27])=[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])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68702819HCID 68702819, compound

Product 1

HCID 68705918HCID 68705918, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(1-cyanocyclopentyl)benzoate (0.17 g, 0.31 mmol) and LiOH.H2O (65 mg, 1.55 mmol) in 8.1 mL THF and 3.1 mL H2O was stirred at rt overnight. The reaction was concentrated, diluted with H2O, made acidic with 10% citric acid solution and extracted with EtOAc. The combined organic layers were washed with brine. Drying and solvent evaporation gave 3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(1-cyanocyclopentyl)benzoic acid. 1H NMR (400 MHz, CDCl3) δ 8.62 (bs, 1H), 8.36 (d, J=1.4 Hz, 2H), 7.28 (m, 3H), 7.09 (d, J=5.7 Hz, 2H), 5.22 (bs, 1H), 3.61 (d, J=13.4 Hz, 1H), 3.43 (m, 1H), 2.60 (m, 2H), 2.20-2.01 (m, 6H), 1.75 (s, 3H), 1.42 (s, 9H).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customDrying
  6. customsolvent evaporation

Sources & evidence

ORD record
ord-bcecbd2b12064e538a66cebb70255f47
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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