Sodium Hydroxide → HCID 67384316, compound

HRID 2360980Notes

Reaction equation

HRID 2360980 reaction equation
C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2([C:34](=[O:42])[NH:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:16][CH2:15][N:14]([C:17](=[O:33])[CH:18]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1.CO>[C:29]([O:28][C:26]([NH:25][C@@H:18]([CH2:19][C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)[C:17]([N:14]1[CH2:15][CH2:16][C:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:43])=[O:2])=[CH:9][CH:8]=2)([C:34](=[O:42])[NH:35][CH:36]2[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]2)[CH2:12][CH2:13]1)=[O:33])=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67384931HCID 67384931, compound

Product 1

HCID 67384316HCID 67384316, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[1-(2-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl)-4-cyclohexylcarbamoyl-piperidin-4-ylmethyl]-benzoic acid methyl ester (4.46 mmol; 2.73 g) in THF (30 mL) and methanol (10 mL) was added a 1M solution of sodium hydroxide (6.69 mmol; 6.69 mL) and the resulting mixture was stirred overnight at room temperature. The resulting mixture was then evaporated and water (20 mL) was added. A 1N hydrochloric acid solution (10 mL) was added dropwise. A precipitate formed that was separated via filtration to yield 4-[1-(2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl)-4-cyclohexylcarbamoyl-piperidin-4-ylmethyl]-benzoic acid after drying. MS (ESI) m/z 598.23 [M+H]+.

Workup

  1. customThe resulting mixture was then evaporated
  2. additionwater (20 mL) was added
  3. additionA 1N hydrochloric acid solution (10 mL) was added dropwise
  4. customA precipitate formed
  5. customthat was separated via filtration

Sources & evidence

ORD record
ord-5bc990fea4854e6582abb5cb738152f5
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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