Methanol → HCID 53695482, compound

HRID 2228582Notes

Reaction equation

HRID 2228582 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12](=[N:45][C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]([NH:21][C:22]2[C:23]([NH:32][C:33](=[O:44])[C:34]3[CH:39]=[CH:38][C:37]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:36][CH:35]=3)=[CH:24][C:25]([C:28]([O:30]C)=[O:29])=[CH:26][CH:27]=2)=[O:20])[CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O1CCOCC1.[OH-].[Na+]>O>[CH2:49]([O:48][C:46]([NH:45][C:12](=[N:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]([NH:21][C:22]2[C:23]([NH:32][C:33](=[O:44])[C:34]3[CH:35]=[CH:36][C:37]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:38][CH:39]=3)=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=2)=[O:20])[CH2:14]1)=[O:47])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 69820033HCID 69820033, compound

Product 1

HCID 53695482HCID 53695482, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N1-[[1-(benzyloxycarbonylamino(benzyloxycarbonylimino)methyl)piperidin-3-yl]carbonyl]-N2-(4-t-butylbenzoyl)-4-methoxycarbonyl-1,2-benzenediamine (0.7 g, 0.94 mmol), CH3OH (10 mL), dioxane (10 mL), and water (6 mL) was added 1 N NaOH (3.7 mL, 3.7 mmol). The reaction was stirred for 48 h and was concentrated. The residue was partitioned between H2O (100 mL) and Et2O (100 mL). The aqueous layer was extracted with Et2O (100 mL), acidified to pH 2.5 with 5 N HCl and extracted with EtOAc (3×200 mL). The combined EtOAc layers were washed with water, MgSO4 dried, concentrated and crystallized at 0° C. overnight to give the title compound as a solid (0.63 g, 92%); TLC: Rf=0.38 (1:15: 135 acetic acid:methanol:chloroform); NMR (CDCl3) δ1.35 (s,9H), 1.50-2.05 (m, 8H), 3.20-3.40 (m, 1N), 3.60-4.05 (m, 3H), 5.05 (s, 4H), 7.20-7.35 (m, 12H), 7.40-7.50 (m, 2H), 7.55-7.65 (m, 1H), 7.90-8.00 (m, 2H), 8.05-8.15 (m, 1H); MS(FAB): 734 (MH+).

Workup

  1. concentrationwas concentrated
  2. customThe residue was partitioned between H2O (100 mL) and Et2O (100 mL)
  3. extractionThe aqueous layer was extracted with Et2O (100 mL)
  4. extractionextracted with EtOAc (3×200 mL)
  5. washThe combined EtOAc layers were washed with water, MgSO4
  6. customdried
  7. concentrationconcentrated
  8. customcrystallized at 0° C. overnight

Sources & evidence

ORD record
ord-51335caf3a094c6e8d45b377a66b01b5
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

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