Dimethylformamide → Ammonium Hydroxide

HRID 1045512Notes

Reaction equation

HRID 1045512 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][C:16]([NH:24][C:25]([O:27]C(C)(C)C)=[O:26])(C(O)=O)[CH2:15]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].CCN([CH:40]([CH3:42])[CH3:41])C(C)C.[C:43]([O-])(O)=O.[Na+].C[N:49]([CH:51]=[O:52])C>>[NH4+:11].[OH-:8].[C:40]([N:24]([C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[CH2:20][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:51]([NH2:49])=[O:52])[CH2:13]2)[C:25](=[O:26])[O-:27])([CH3:41])([CH3:42])[CH3:43]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 67390064HCID 67390064, compound

Product 2

HCID 14923Ammonium HydroxideHCID 131730921HCID 131730921, compound

Procedure

A solution of (±)-5-{[(benzyloxy)carbonyl]amino)-2-tert-butoxycarbonyl)amino]indane-2-carboxylic acid from Step B (829 mg, 1.94 mmol), ammonium chloride (208 mg, 3.89 mmol), pyBOP (1.52 g, 2.92 mmol), and DIEA (1.35 mL, 7.78 mmol) in DMF (3 mL) was stirred at ambient temperature for 16 h. The reaction mixture was poured onto saturated NaHCO3 (20 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 90:9:1, to give the title compound, MS: m/z=426 (M+1).

Workup

  1. extractionextracted with CH2Cl2 (3×20 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-f8b27d2c18d34d87b55629c9d5cc563a
Source dataset
uspto-grants-2013_10
Patent number
US08569291B2

Reaction notes

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