Tetrahydrofuran → HCID 68568949, compound

HRID 1867597Notes

Reaction equation

HRID 1867597 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:15](N(CC)CC)C.[Si:22]([O:39][CH2:40][C@@H:41]([C:43]([O:45]C)=[O:44])[NH2:42])([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[O:47]1CCC[CH2:48]1>>[CH3:15][N:42]([C:48]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)=[O:47])[C@H:41]([C:43]([OH:45])=[O:44])[CH2:40][O:39][Si:22]([C:35]([CH3:38])([CH3:36])[CH3:37])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471Triethylamine2×HCID 12682914-Amino-1-Boc-piperidineHCID 11210526HCID 11210526, compound

Product 1

HCID 68568949HCID 68568949, compound

Procedure

4-Amino-1-boc-piperidine (770 mg, 3.85 mmol) and triethylamine (0.536 mL, 3.85 mmol) in tetrahydrofuran (5 mL) was added to a solution of p-nitrophenylchloroformate (775 mg, 3.85 mmol) in tetrahydrofuran (15 mL) at 0° C. After 1 h, additional triethylamine was added (1.07 mL, 7.7 mmol) along with methyl O-[tert-butyl(diphenyl)silyl]serinate (1.38 g, 3.85 mmol). The reaction warmed to ambient temperature and was then heated to 50° C. After 16 h, the mixture was concentrated and redissolved in ethyl acetate. The ethyl acetate layer was washed with saturated sodium bicarbonate solution (3×), water, brine, and dried over sodium sulfate. Purification by silica gel chromatography (100% dichloromethane→8% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (1.8 g). MS 584.62 (M+1)

Workup

  1. temperaturewas then heated to 50° C
  2. waitAfter 16 h
  3. concentrationthe mixture was concentrated
  4. dissolutionredissolved in ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated sodium bicarbonate solution (3×), water, brine
  6. dry with materialdried over sodium sulfate
  7. customPurification by silica gel chromatography (100% dichloromethane→8% methanol {1% ammonium hydroxide}/dichloromethane)

Sources & evidence

ORD record
ord-236be44477564e0d93cfb67eca250530
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

Loading…