Hexamethyldisilazane → HCID 59468965, compound

HRID 1690085Notes

Reaction equation

HRID 1690085 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][CH:25]=3)=[CH:18][CH:17]=2)[CH2:14][CH2:13][C@@:9]1([CH3:30])[C:10](O)=[O:11])=[O:7])([CH3:4])[CH3:3].C([N:34](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>[NH2:34][C:10]([C@:9]1([CH3:30])[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][CH:25]=3)=[CH:18][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 59468933HCID 59468933, compound

Product 1

HCID 59468965HCID 59468965, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (5R)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-2-methyl-5-{4-[(phenylmethyl)oxy]phenyl}-L-proline (D8, 870 mg, 2.11 mmol), diisopropylethyl amine (0.74 ml, 4.22 mmol) and TBTU (814 mg, 2.53 mmol) in dry DMF (8 ml) was stirred for 15 min at room temperature. HMDS (0.70 ml, 3.17 mmol) was added and stirring was continued at room temperature overnight. The mixture was cooled to 0° C. and saturated aqueous NaHCO3 solution was added. 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 (7:3) to afford the title compound (857 mg, 99%); Rt (HPLC): 5.85 min; MS: (ES/+) m/z: 433 [M+Na+]; C24H30N2O4 requires 410; Rf (cyclohexane:ethyl acetate=6:4): 0.32.

Workup

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

Sources & evidence

ORD record
ord-2e0436485c1b494fa0344847a16dffeb
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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