Water → HCID 22054690, compound

HRID 1829716Notes

Reaction equation

HRID 1829716 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[C:5]([C:10]([O:12]C)=[O:11])=[CH:4][C:3]=1[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:16][CH2:15]1.O.[Li+].[OH-]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[C:5]([C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 22054696HCID 22054696, compound

Product 1

HCID 22054690HCID 22054690, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-fluoro-4-methylthio-5-methoxycarbonylphenyl)-N-Cbz-piperidine (1.38 g) dissolved in 100 mL 1:1 THF:H2O was added 0.45 g LiOH. Mixture was stirred for 18 h, THF was evaporated, residue was mixed with 25 mL 1N HCl, and extracted with DCM (3×50 mL). Extracts were combined, dried over Na2SO4, and evaporated to give 1.33 g product; MS m/z 404 (M+H); 1H NMR (CDCl3) δ 8.01 (d), 7.45-7.25 (m), 6.94 (d), 5.17 (s), 4.50-4.21 (m), 2.99 (tt), 3.01-2.78 (m), 2.44 (s), 1.84 (dm), 1.69 (qd).

Workup

  1. customTHF was evaporated
  2. additionresidue was mixed with 25 mL 1N HCl
  3. extractionextracted with DCM (3×50 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-b99dd04081d34a808884a77c0066771f
Source dataset
uspto-grants-2006_06
Patent number
US07064136B2

Reaction notes

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