1,2-Dichloroethane → Ammonium Hydroxide

HRID 1045515Notes

Reaction equation

HRID 1045515 reaction equation
C([O:5]C(=O)[NH:7][C:8]1([C:20]([NH2:22])=[O:21])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:17]([O-:19])=[O:18])[CH:14]=2)[CH2:9]1)(C)(C)C.C(OC(NC1(C(O)=O)CC2C(=CC=C([N+]([O-])=O)C=2)C1)=O)(C)(C)C.[Cl-].[NH4+].C(Cl)CCl.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH4+:7].[OH-:5].[NH2:7][C:8]1([C:20]([NH2:22])=[O:21])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:17]([O-:19])=[O:18])[CH:14]=2)[CH2:9]1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 166383322-[[(1,1-Dimethylethoxy)carbonyl]amino]-2,3-dihydro-5-nitro-1H-indene-2-carboxylic acidHCID 131730923HCID 131730923, compound

Product 2

HCID 14923Ammonium HydroxideHCID 58432797HCID 58432797, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-tert-Butyl[2-(aminocarbonyl)-5-nitro-2,3-dihydro-1H-inden-2-yl]carbamate A solution of (±)-2-[(tent-butoxycarbonyl)amino]-5-nitroindane-2-carboxylic acid from Step C (470 mg, 1.46 mmol), ammonium chloride (156 mg, 2.92 mmol), EDC (419 mg, 2.19 mmol), HORT (335 mg, 2.19 mmol), and DIEA (1.27 mL, 7.29 mmol) in DMF (5 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=322 (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-7a700090897a4f2095cdf07414146f4c
Source dataset
uspto-grants-2013_10
Patent number
US08569291B2

Reaction notes

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