tert-Butyldimethylsilyl chloride → HCID 86602441, compound

HRID 1242816Notes

Reaction equation

HRID 1242816 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:17][C@H:16]([OH:18])[CH2:15][C@H:10]2[C:11]([O:13][CH3:14])=[O:12])=[O:8])=[CH:3][CH:2]=1.[CH3:25][C:26]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])[CH3:27]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:17][C@H:16]([O:18][Si:29]([C:26]([CH3:28])([CH3:27])[CH3:25])([CH3:31])[CH3:30])[CH2:15][C@H:10]2[C:11]([O:13][CH3:14])=[O:12])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chloride2×HCID 58585501HCID 58585501, compound2×

Product 1

HCID 86602441HCID 86602441, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl (4R)-1-(1,1′-biphenyl-4-ylcarbonyl)-4-hydroxy-L-prolinate (intermediate 2a, 2.07 g, 6.35 mmol) was dissolved in DCM (30 ml) and treated with 4-DMAP (776 mg, 6.35 mmol), TEA (2.21 ml, 15.88 mmol) and TBDMS-Cl (1.91 g, 12.7 mmol). The reaction was monitored by LC/MS. After 24 h, as the reaction was not completed, TBDMS-CL (300 mg, 2 mmol) and TEA (1 ml) were added. After 48 h, the reaction was completed. The mixture was washed with sat. NH4Cl and brine (twice), dried over magnesium sulfate, filtered and concentrated. The crude (2.85 g) was purified by flash chromatography using EtOAc/cHex 50:50 as eluant.

Workup

  1. waitAfter 48 h
  2. washThe mixture was washed with sat. NH4Cl and brine (twice),
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude (2.85 g) was purified by flash chromatography

Sources & evidence

ORD record
ord-286759ba81b94cde98f16d377f2a5cdd
Source dataset
uspto-grants-2006_10
Patent number
US07115754B2

Reaction notes

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