Triethylamine → HCID 21072812, compound

HRID 1867336Notes

Reaction equation

HRID 1867336 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]([CH3:31])([CH3:30])[CH2:11][CH2:12][N:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([CH2:26][CH2:27][CH3:28])([CH2:23][CH2:24][CH3:25])[O:15][C:14]1=[O:29].[CH2:32]([O:39][C:40]1[CH:41]=[C:42]([C:51](=[O:57])[CH:52](OCC)O)[C:43]2[O:48][CH2:47][C:46](=[O:49])[NH:45][C:44]=2[CH:50]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[BH4-].[Li+]>C1COCC1.ClCCl.O>[CH2:32]([O:39][C:40]1[CH:41]=[C:42]([CH:51]([OH:57])[CH2:52][NH:9][C:10]([CH3:30])([CH3:31])[CH2:11][CH2:12][N:13]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]([CH2:26][CH2:27][CH3:28])([CH2:23][CH2:24][CH3:25])[O:15][C:14]2=[O:29])[C:43]2[O:48][CH2:47][C:46](=[O:49])[NH:45][C:44]=2[CH:50]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 4148881Lithium borohydrideHCID 21072820HCID 21072820, compoundHCID 22063474HCID 22063474, compound

Product 1

HCID 21072812HCID 21072812, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

86 μL (0.619 mmol) of triethylamine is added to a solution of 200 mg (0.564 mmol) of 1-(3-amino-3-methylbutyl)-4,4-dipropyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one hydrochloride in absolute THF (5 mL) at RT under a nitrogen atmosphere and the mixture is stirred for 30 minutes, 200 mg (0.560 mmol) of 6-benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one is added and the mixture is stirred for another 2 h at RT. The mixture is cooled to 10° C., combined with 51 mg (2.34 mmol) of lithium borohydride, heated to RT, and stirred for 1 hour at RT. It is again cooled to 10° C. and slowly combined with 15 mL water and 20 mL dichloromethane. The phases are separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried with sodium sulfate and evaporated down in vacuo. The residue is dissolved in EtOAc (8 mL) and acidified to pH 2 by the addition of HCl solution (saturated in EtOAc). The precipitate formed is filtered off, washed with EtOAc and dried in vacuo. Yield: 270 mg (74%; hydrochloride), HPLC-MS: Rt=18.7 min. (method A).

Workup

  1. stirringthe mixture is stirred for another 2 h at RT
  2. temperatureheated to RT
  3. stirringstirred for 1 hour at RT
  4. temperatureIt is again cooled to 10° C.
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with dichloromethane
  7. dry with materialThe combined organic phases are dried with sodium sulfate
  8. customevaporated down in vacuo
  9. dissolutionThe residue is dissolved in EtOAc (8 mL)
  10. additionacidified to pH 2 by the addition of HCl solution (saturated in EtOAc)
  11. customThe precipitate formed
  12. filtrationis filtered off
  13. washwashed with EtOAc
  14. customdried in vacuo

Sources & evidence

ORD record
ord-248898c12dd44036b65d7b088819354d
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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