Ammonia → HCID 86651606, compound

HRID 1372911Notes

Reaction equation

HRID 1372911 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]([O:9][C:10](=[O:32])[NH:11][C:12]([CH3:31])([CH3:30])[CH2:13][CH2:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([OH:29])([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.N>CCOC(C)=O.C1COCC1>[CH3:31][C:12]([NH:11][C:10](=[O:32])[O:9][C:5]([CH3:6])([CH3:7])[CH3:8])([CH3:30])[CH2:13][CH2:14][N:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH3:28])[O:29][C:1]1=[O:2]

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) phosgene solution (20 wt. % in toluene) are slowly added dropwise at 0° C. to a solution of 6.00 g (15.28 mmol) tert-butyl{3-[2-(1-hydroxy-1-propyl-butyl)-phenylamino]-1,1-dimethyl-propyl}-carbamate and 5.32 mL (38.21 mmol) triethylamine in abs. THF (80 mL). The mixture is stirred for 2 h at RT, diluted with EtOAc, combined with ice and made basic with sat. aqueous ammonia solution. The aqueous phase is exhaustively extracted with EtOAc and the combined org. phases are washed with saturated aqueous NaCl, dried with sodium sulphate and evaporated down i. vac. 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. washphases are washed with saturated aqueous NaCl
  3. dry with materialdried with sodium sulphate
  4. customevaporated down i
  5. customAfter column chromatography (silica gel, cyclohexane/EtOAc 6:1) the product is obtained as a yellow oil

Sources & evidence

ORD record
ord-a86e204d4d5d474d9831e881edceb45e
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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