Thionyl Chloride → HCID 178445070, compound

HRID 1296525Notes

Reaction equation

HRID 1296525 reaction equation
O.[NH:2]1[C:6]([CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][CH:16]3[CH:11]([CH2:12][CH:13]([C:19]([OH:21])=[O:20])[NH:14][CH2:15]3)[CH2:10]2)=[N:5][N:4]=[N:3]1.S(Cl)(Cl)=O>C(C(CC)CO)C>[CH2:8]([CH:9]([CH2:10][CH3:11])[CH2:18][O:20][C:19]([CH:13]1[CH2:12][CH:11]2[CH:16]([CH2:17][CH2:18][CH:9]([CH2:8][CH2:7][C:6]3[NH:2][N:3]=[N:4][N:5]=3)[CH2:10]2)[CH2:15][NH:14]1)=[O:21])[CH3:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178526951HCID 178526951, compound

Product 1

HCID 178445070HCID 178445070, compound

Reagents, catalysts & solvents 1

HCID 73582-Ethyl-1-butanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2.5 g (8.4 mmol) of 6-[2-(1H-Tetrazol-5-yl)-ethyl]-decahydro-isoquinoline-3-carboxylic acid monohydrate (prepared as described in J. Med. Chem., 39 (11), pp. 2232-2244, (1996) or U.S. Pat. No. 5,670,516 (issued Sep. 23, 1997)) in 20 ml of 2-ethyl-1-butanol, 6.8 ml (92.8 mmol) of thionyl chloride is added. The solution is stirred at 120° C. for 3 hr. The mixture is concentrated in vacuo and the residue washed with ethyl ether. The residue is purified by SPE (Oasis HLB) to afford the title compound.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. washthe residue washed with ethyl ether
  3. customThe residue is purified by SPE (Oasis HLB)

Sources & evidence

ORD record
ord-4b2ca85557d341c6b972c7becec9835f
Source dataset
uspto-grants-2007_07
Patent number
US07247644B2

Reaction notes

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