Hydrochloric Acid → HCID 58748275, compound

HRID 1162617Notes

Reaction equation

HRID 1162617 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[CH2:7]1)C.[OH-].[Na+].Cl.C1(C)C=CC=CC=1>C(O)C>[Cl:20][C:17]1[S:16][C:15]([C:13]([NH:12][CH:8]2[CH2:9][CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:21])=[O:3])[CH2:7]2)=[O:14])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14798Sodium HydroxideHCID 58748316HCID 58748316, compound

Product 1

HCID 58748275HCID 58748275, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.2 To a stirred solution of {3-[(5-chloro-thiophene-2-carbonyl)-amino]-piperidin-1-yl}-acetic acid ethyl ester at r.t. in 5 ml ethanol were added 5 ml 1 N NaOH. The slurry slowly turned to a clear solution. Stirring at r.t. was then continued for 5 h. The mixture was neutralized by adding 5 ml of 1 N HCl (pH ˜7). The light orange solution was concentrated to leave an off-white solid. This residue was coevaporated several times with toluene to remove the remaining H2O, and dried overnight (r.t., 0.5 mbar) to give 1.07 g {3-[(5-chloro-thiophene-2-carbonyl)-amino]-piperidin-1-yl}-acetic acid (containing 2 mol equivalents of sodium chloride). Off-white solid. MS 301.3 ([M−H]−)

Workup

  1. concentrationThe light orange solution was concentrated
  2. customto leave an off-white solid
  3. customto remove the remaining H2O
  4. customdried overnight (r.t., 0.5 mbar)

Sources & evidence

ORD record
ord-0ae775178b8e4f5184badae0857c931a
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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