Hydrochloric Acid → HCID 66616074, compound

HRID 2367057Notes

Reaction equation

HRID 2367057 reaction equation
[CH3:1][C:2]1([CH3:37])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:35])[C@@H:18]([NH:27]C(=O)OC(C)(C)C)[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)[C:3]1=[O:36].Cl.[Cl:39][Si](C)(C)C.CO>C(OCC)C>[ClH:39].[NH2:27][C@@H:18]([CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:17]([N:14]1[CH2:13][CH2:12][CH:11]([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:37])([CH3:1])[C:3]2=[O:36])[CH2:16][CH2:15]1)=[O:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 66615885HCID 66615885, compound

Product 1

HCID 66616074HCID 66616074, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (S)-tert-butyl 1-(4-(3,3-dimethyl-2-oxoindolin-1-yl)piperidin-1-yl)-1-oxo-4-phenylbutan-2-ylcarbamate (2.79 g, 5.52 mmol, EXAMPLE 1, Step 3) and 1 mol/L hydrochloride in diethyl ether (25 mL) was stirred at room temperature. After 4 h, a mixture of chlorotrimethylsilane (2 mL) and methanol (4 mL) was added to the reaction suspension. The whole mixture changed to a clear solution and was stirred for 3 h. The mixture was concentrated in vacuo and the residue was diluted with diethyl ether and re-concentrated to remove methanol completely. The obtained solid was washed with diethyl ether to give the title compound (2.05 g, 84%).

Workup

  1. additionwas added to the reaction suspension
  2. stirringwas stirred for 3 h
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe residue was diluted with diethyl ether
  5. concentrationre-concentrated
  6. customto remove methanol completely
  7. washThe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-58a10e4b3f4847d4ad0a76a965a4b16d
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

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