tert-Butyldimethylsilyl chloride → HCID 131734788, compound

HRID 1777962Notes

Reaction equation

HRID 1777962 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:18][O:19][CH:20]([O:39][CH3:40])[C:21]1[C:30]([CH2:31][N:32]2[CH2:36][CH2:35][C@H:34]([OH:37])[C:33]2=[O:38])=[CH:29][C:28]2[CH2:27][CH2:26][CH2:25][NH:24][C:23]=2[N:22]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(Cl)Cl>[Si:1]([O:37][C@H:34]1[CH2:35][CH2:36][N:32]([CH2:31][C:30]2[C:21]([CH:20]([O:39][CH3:40])[O:19][CH3:18])=[N:22][C:23]3[NH:24][CH2:25][CH2:26][CH2:27][C:28]=3[CH:29]=2)[C:33]1=[O:38])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 118036900HCID 118036900, compound2×

Product 1

HCID 131734788HCID 131734788, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyldimethylsilyl chloride (3.77 g, 25.02 mmol), DIPEA (4.84 ml, 27.7 mmol) and DMAP (51 mg, 0.42 mmol) were added to a solution of (S)-1-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-3-hydroxypyrrolidin-2-one (intermediate 103A, 6.7 g, 20.85 mmol) in DMF (15 ml) and DCM (60 ml) at 0° C. The reaction mixture was stirred for 2 days at room temperature, partitioned between water and DCM, the organic layers washed with saturated aqueous NaHCO3, dried over Na2SO4 and evaporated to give the title compound as a brown glass. (UPLC-MS 6) tR 0.94; ESI-MS 436.2 [M+H]+.

Workup

  1. custompartitioned between water and DCM
  2. washthe organic layers washed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-e0cacfc41ba74b0e855de0ddae261c0b
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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