Ammonia → HCID 86651606, compound

HRID 1867330Notes

Reaction equation

HRID 1867330 reaction equation
[C:1](Cl)(Cl)=[O:2].[OH:5][C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][CH2:20][CH2:21][C:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:24])[CH3:23])([CH2:10][CH2:11][CH3:12])[CH2:7][CH2:8][CH3:9].C(N(CC)CC)C.N>C1COCC1.CCOC(C)=O>[C:28]([O:27][C:26](=[O:32])[NH:25][C:22]([CH3:23])([CH3:24])[CH2:21][CH2:20][N:19]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:6]([CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH3:12])[O:5][C:1]1=[O:2])([CH3:30])([CH3:29])[CH3:31]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6371PhosgeneHCID 8471TriethylamineHCID 86600980Tert-butyl {3-[2-(1-hydroxy-1-propylbutyl)phenylamino]-1,1-dimethylpropyl}carbamate

Product 1

HCID 86651606HCID 86651606, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8.85 mL (16.81 mmol) of phosgene solution (20 wt. % in toluene) is slowly added dropwise at 0° C. to a solution of 6.00 g (15.28 mmol) of tert-butyl {3-[2-(1-hydroxy-1-propylbutyl)phenylamino]-1,1-dimethylpropyl}carbamate and 5.32 mL (38.21 mmol) of triethylamine in absolute THF (80 mL). The mixture is stirred for 2 hours at RT, diluted with EtOAc, combined with ice, and made basic with saturated aqueous ammonia solution. The aqueous phase is exhaustively extracted with EtOAc and the combined organic phases are washed with saturated aqueous NaCl, dried with sodium sulfate, and evaporated down in vacuo. After column chromatography (silica gel, cyclohexane/EtOAc 6:1) the product is obtained as a yellow oil. Yield: 4.57 g (71%).

Workup

  1. extractionThe aqueous phase is exhaustively extracted with EtOAc
  2. washthe combined organic phases are washed with saturated aqueous NaCl
  3. dry with materialdried with sodium sulfate
  4. customevaporated down in vacuo
  5. customAfter column chromatography (silica gel, cyclohexane/EtOAc 6:1) the product is obtained as a yellow oil

Sources & evidence

ORD record
ord-bb40f34fc136417cb756bfccf000e995
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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