Diisopropylethylamine → HCID 57495554, compound

HRID 1092347Notes

Reaction equation

HRID 1092347 reaction equation
[NH2:1][C:2]1([CH2:7][NH:8][CH:9]2[CH:16]3[CH2:17][C:12]4([OH:20])[CH2:13][C:14]([OH:19])([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.Cl[C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1>[OH:19][C:14]12[CH2:15][CH:16]3[CH2:17][C:12]([OH:20])([CH2:11][CH:10]([CH:9]3[N:8]3[CH2:7][C:2]4([CH2:6][CH2:5][CH2:4][CH2:3]4)[NH:1][C:31]3=[O:33])[CH2:18]1)[CH2:13]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 57495632HCID 57495632, compound

Product 1

HCID 57495554HCID 57495554, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-[(1-amino-cyclopentylmethyl)-amino]-adamantane-1,3-diol (250 mg, obtained in examples 122, step B) and N,N-diisopropylethylamine (0.62 ml) in CH2Cl2 (3.0 ml), a solution of triphosgene (90 mg) in THF (1 ml) was added dropwise at room temperature. The mixture was stirred at room temperature for 2 hr. The mixture was poured into saturated NaHCO3 solution, and extracted with AcOEt. The organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was triturated with CH2Cl2 to obtain the title compound (100 mg, 37%) as a white solid. MS (ESI): 307.1 (MH+).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was triturated with CH2Cl2

Sources & evidence

ORD record
ord-773ad85d017f47a896d4eb0872ef500d
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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