Water → HCID 53893975, compound

HRID 2228581Notes

Reaction equation

HRID 2228581 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1.[OH-].[Na+].[CH2:12]([O:19][C:20]([NH:22][C:23](=[N:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])SC)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>O1CCOCC1.CCOCC>[CH2:30]([O:29][C:27]([NH:26][C:23](=[N:22][C:20]([O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:21])[N:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1)=[O:28])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 962WaterHCID 4498Nipecotic AcidHCID 14798Sodium HydroxideHCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothiourea

Product 1

HCID 53893975HCID 53893975, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of nipecotic acid (1.66 g, 12.8 mmol) in 2 N NaOH (12.8 mL, 25.6 mmol) and dioxane (30 mL) was added 1,3-bis(benzyloxycarbonyl)-2-methyl-2-thiopseudourea (4.6 g, 12.8 mmol). After 48 h, the reaction mixture was added to H2O (200 mL) and Et2O (200 mL). The aqueous layer was separated and extracted with Et2O (2×200 mL). The aqueous layer was acidified to pH 2.0 with 3 N HCl and extracted with EtOAc (500 mL). The organic layer was MgSO4 dried and concentrated to give the title compound (4.0 g, 71%): TLC Rf=0.65 (1:15: 135 Acetic Acid:Methanol:Chloroform); NMR (CDCl3) δ1.55-1.92 (m, 6H), 2.00-2.15 (m, 1H), 2.70-2.80 (m, 1H), 3.20-3.35 (q, 1H), 3.38-3.45 (m, 1H), 3.75-4.10 (m, 1H), 5.10 (s, 2H), 5.22 (s, 2H), 7.30-7.40 (m, 10H); FD-MS 440 (MH+).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with Et2O (2×200 mL)
  3. extractionextracted with EtOAc (500 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b460997ffa8468d8aa66ca3888d8fe5
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

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