Hydrochloric Acid → HCID 23456812, compound

HRID 1874952Notes

Reaction equation

HRID 1874952 reaction equation
CC([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15](C(OCCC(C)(C)C)=O)[C:14]([C:28]([O-:30])=[O:29])=[CH:13]2)(C)C.Cl.[C:34](O)([C:36](F)(F)F)=O>C1COCC1>[OH:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:28]([O:30][CH2:34][CH3:36])=[O:29])=[CH:13]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 86761647HCID 86761647, compound

Product 1

HCID 23456812HCID 23456812, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(1,1-dimethylethyl)2-ethyl 5-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]-1H-indole-1,2-dicarboxylate (0.389 g, 0.840 mmol) in THF (4 mL) was treated with 1N HCl (0.840 mL, 0.840 mmol) and the reaction mixture was stirred for several hours at room temp. TLC showed consumption of the starting material and 2 product spots. Solvents were evaporated and the residue dissolved in DCM (4 mL) and TFA (0.25 mL, 3.24 mmol) was added. TLC showed a single product spot. The solvents were evaporated to afford the title compound (0.224 g, 96%) as a grey solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 10.74 (br. s., 1H), 7.41 (d, 1H), 7.32 (s, 1H), 7.12 (d, 1H), 7.06 (d, 1H), 6.94 (dd, 1H), 4.32 (q, 2H), 4.05 (t, 2H), 3.88 (t, 2H), 1.32 (t, 3H). LCMS: m/z 204.2 (M-45).

Workup

  1. customconsumption of the starting material and 2 product spots
  2. customSolvents were evaporated
  3. dissolutionthe residue dissolved in DCM (4 mL)
  4. customThe solvents were evaporated

Sources & evidence

ORD record
ord-9b701ef67a574488ad52ec40b06e884a
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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