1,2-Dichloroethane → HCID 178504579, compound

HRID 1499389Notes

Reaction equation

HRID 1499389 reaction equation
[C:1]([N-:5][O:6][SiH:7]([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[NH:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13].OCCCCCC(O)=O.C(Cl)CCl.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl.CO>[OH:6][NH-:5].[C:1]([N-:5][O:6][SiH:7]([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[NH:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 144906-Hydroxyhexanoic AcidHCID 757711-HydroxybenzotriazoleHCID 131731289HCID 131731289, compound2×

Product 1

HCID 178504579HCID 178504579, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

An anhydrous dichloromethane solution was prepared by mixing the thus-obtained t-butyl-dimethyl siloxy amide-L-proline (Compound 19) (550 mg, 1.8 mmol), 6-hydroxyhexanoic acid (300 mg, 2.3 mmol), EDC (434 mg, 2.3 mmol), and 1-hydroxybenzotriazole (695 mg, 4.5 mmol) in anhydrous dichloromethane (20 ml). Triethylamine (689 mg, 6.8 mmol) was added to this solution at room temperature in an argon atmosphere, and then, this was stirred overnight at room temperature in an argon atmosphere. The mixture was washed with saturated saline. An organic layer was collected, and the collected organic layer was dried with sodium sulfate. Thereafter, the organic layer was filtered. The solvent in the filtrate obtained was removed by evaporation under reduced pressure. The residual substance obtained was applied to silica gel column chromatography (the eluent: CH2Cl2:CH3OH=9:1). Thus, Compound 20 in the form of colorless syrup was obtained (696 mg, yield: 92%). The result of NMR analysis with respect to this compound is shown below.

Workup

  1. washThe mixture was washed with saturated saline
  2. customAn organic layer was collected
  3. dry with materialthe collected organic layer was dried with sodium sulfate
  4. filtrationThereafter, the organic layer was filtered
  5. customThe solvent in the filtrate obtained
  6. customwas removed by evaporation under reduced pressure
  7. customThe residual substance obtained

Sources & evidence

ORD record
ord-816ea7f8b3d842c8865287c0706226ce
Source dataset
uspto-grants-2015_12
Patent number
US09200278B2

Reaction notes

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