Lithium Hydroxide → 2-[3-(Benzyloxycarbonylamino-methyl)-piperidin-1-yl]-thiazole-4-carboxylic acid

HRID 460211Notes

Reaction equation

HRID 460211 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][NH:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:12]2)[S:9][CH:10]=1)=[O:5])C.[Li+].[OH-]>C1COCC1>[CH2:22]([O:21][C:19]([NH:18][CH2:17][CH:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:8]2[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[CH2:12]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 694109422-[3-(Benzyloxycarbonylamino-methyl)-piperidin-1-yl]-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 187717272-[3-(Benzyloxycarbonylamino-methyl)-piperidin-1-yl]-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[3-(benzyloxycarbonylamino-methyl)-piperidin-1-yl]-thiazole-4-carboxylic acid ethyl ester (439 mg, 1.15 mmol) in THF (5 mL) at RT, a 1M solution of LiOH (aq) (1.72 mL, 1.72 mmol) was added. After 16 h the solvent was evaporated in vacuo. The residue was treated with brine (25 mL) and acidified to pH 1 with 2N HCl (aq) then extracted with EtOAc (30 mL). The organic layer was separated, dried over Na2SO4, filtered and the solvent evaporated in vacuo to yield the title compound as a colorless oil. MS m/z: 355.9 (M+H). Calc'd. for C16H25N3O4S-355.45.

Workup

  1. customAfter 16 h the solvent was evaporated in vacuo
  2. additionThe residue was treated with brine (25 mL)
  3. extractionthen extracted with EtOAc (30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-5f0344506f4d4b1dbe81860075eb70b0
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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