Triethylamine → HCID 66975750, compound

HRID 1022715Notes

Reaction equation

HRID 1022715 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2[CH2:23][NH:24][CH2:25][C:26](OCC)=[O:27])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:31]([Si](C)(C)C)=[C:32]=[O:33].C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:11][C@H:10]2[CH2:23][N:24]2[CH2:25][C:26](=[O:27])[NH:31][C:32]2=[O:33])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 70696Trimethylsilyl isocyanate2×HCID 66975611HCID 66975611, compound

Product 1

HCID 66975750HCID 66975750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (1.9 mL) of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[(2-ethoxy-2-oxoethyl)amino]methyl}-1,4-oxazepane-4-carboxylate (180 mg) in THF were added isocyanatotrimethylsilane (0.078 mL) and triethylamine (0.082 mL), and the mixture was stirred at room temperature for 2 hr. Then, isocyanatotrimethylsilane (0.156 ml) and triethylamine (0.164 mL) were added, and the mixture was stirred at 50° C. for 2 hr, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate). The obtained residue was diluted with methanol (1.4 mL), triethylamine (0.080 ml) was added, and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (115 mg).

Workup

  1. stirringthe mixture was stirred at 50° C. for 2 hr
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)
  4. additionThe obtained residue was diluted with methanol (1.4 mL), triethylamine (0.080 ml)
  5. additionwas added
  6. stirringthe mixture was stirred at 50° C. for 2 hr
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-59881b3c7584495d90f4c1e4ee1aea94
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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