Triethylamine → HCID 22823403, compound

HRID 2166798Notes

Reaction equation

HRID 2166798 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:32][C:33]1[CH:42]=[C:41]2[C:36]([CH:37]=[C:38]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:39](=[O:43])[O:40]2)=[CH:35][CH:34]=1>O1CCCC1>[C:1]([NH:8][C@H:9]([C:14]([NH:32][C:33]1[CH:42]=[C:41]2[C:36]([CH:37]=[C:38]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:39](=[O:43])[O:40]2)=[CH:35][CH:34]=1)=[O:16])[CH2:10][CH:11]([CH3:12])[CH3:13])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 777512H-1-Benzopyran-2-one, 7-amino-3-phenyl-HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 22823403HCID 22823403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.16 g (5 mmol) of Boc-L-leucine and 0.70 ml (5 mmol) of triethylamine in 12 mL of tetrahydrofuran (dried over sodium/lead alloy) at -15° was added 0.66 mL (5 mmol) of i-butyl chloroformate. After 10 min., 1.19 g (5 mmol) of 7-amino-3-phenylcoumarin suspended in 6 mL of tetrahydrofuran was added. The mixture was stirred at -15° for 30 min. and then overnight at room temperature. The reaction mixture was then reduced to dryness on a rotary evaporator at 1.6 kPa and 60°. The residue was taken up in 100 mL of ethyl acetate, washed twice with 25-mL portions of 1 N aqueous sodium bicarbonate and twice with 25-mL portions of saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was dried overnight at room temperature and 3 Pa to yield 1.91 g. (84.8%) of crude product as a yellow foam which was purified by chromatography on a silica gel column eluted first with methylene chloride and then with 5% methanol in methylene chloride. Product recovery was 66.5%.

Workup

  1. additionwas added
  2. customovernight
  3. customat room temperature
  4. customThe reaction mixture was then reduced to dryness on a rotary evaporator at 1.6 kPa and 60°
  5. washwashed twice with 25-mL portions of 1 N aqueous sodium bicarbonate and twice with 25-mL portions of saturated sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was dried overnight at room temperature
  10. custom3 Pa to yield 1.91 g
  11. custom(84.8%) of crude product as a yellow foam which was purified by chromatography on a silica gel column
  12. washeluted first with methylene chloride

Sources & evidence

ORD record
ord-d347c34f5f114fdab5e6d656b9a51cc7
Source dataset
uspto-grants-1983_06
Patent number
US04388233

Reaction notes

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