Hexamethyldisilazane → HCID 59468964, compound

HRID 1690112Notes

Reaction equation

HRID 1690112 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@@H:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[C:18]([O:31][CH3:32])[CH:17]=2)[CH2:14][CH2:13][C@@:9]1([CH3:33])[C:10](O)=[O:11])=[O:7])([CH3:4])[CH3:3].C([N:37](C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C[Si](N[Si](C)(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:37][C:10]([C@:9]1([CH3:33])[CH2:13][CH2:14][C@H:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[C:18]([O:31][CH3:32])[CH:17]=2)[N:8]1[C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])=[O:11]

Participants

7

Reactant 5

HCID 13838HexamethyldisilazaneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59468917HCID 59468917, compound

Product 1

HCID 59468964HCID 59468964, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (5R)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-5-[4-{[(2-fluorophenyl)methyl]oxy}-3-(methyloxy)phenyl]-2-methyl-L-proline (D60, 150 mg, 0.33 mmol), diisopropylethyl amine (0.115 ml, 0.66 mmol) and TBTU (116 mg, 0.36 mmol) in dry DMF (5 ml) was stirred for 15 min at room temperature. HMDS (0.106 ml, 0.5 mmol) was added and stirring was continued at room temperature for 2 h. The mixture was cooled to 0° C. and saturated aqueous NaHCO3 solution was added and the resulting suspension was stirred for 30 min. The mixture was extracted with ethyl acetate and washed three times with ice cold brine. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel using cyclohexane and ethyl acetate (8:2 to 7:3) to afford the title compound (110 mg, 73%); Rt (HPLC): 5.68 min; MS: (ES/+) m/z: 481 [M+Na] C25H31FN2O5 requires 458.

Workup

  1. stirringthe resulting suspension was stirred for 30 min
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed three times with ice cold brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5182b49d47da490fa7a52380f95a972f
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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