Triethylamine → HCID 86592518, compound

HRID 1374407Notes

Reaction equation

HRID 1374407 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C@H:9]([C:21](O)=[O:22])[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.O>[CH2:14]([O:13][C:11]([NH:10][C@@H:9]([CH2:21][OH:22])[CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:24])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 699270851644-83-8

Product 1

HCID 86592518HCID 86592518, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(benzyloxy)carbonyl-D-glutamic acid 5-tert-butyl ester (35 g, 102 mol) in THF (500 ml) was added at −30° C. triethylamine (17 ml, 122 mmol), followed by addition of ethyl chloroformate (12 ml, 122 mmol) and the mixture was stirred at the same temperature. Then to the mixture was added at −30° C. a solution of sodium borohydride (11.6 g, 306 mmol) in water (51 ml) and the mixture was stirred for 30 minutes. Then the solution was raised to 0° C. and stirred for 30 minutes. To the reaction mixture was added water and the solution was extracted three times with ethyl acetate and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and the organic solvent was removed under reduced pressure. The residue was purified by silica gel (210 g) chromatography (Hexane/ethyl acetate: 3/2→1/1) to give tert-butyl (4R)-4-{[(benzyloxy)carbonyl]amino}-5-hydroxypentanoate (16.5 g, 50%).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringstirred for 30 minutes
  3. extractionthe solution was extracted three times with ethyl acetate
  4. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customthe organic solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel (210 g) chromatography (Hexane/ethyl acetate: 3/2→1/1)

Sources & evidence

ORD record
ord-41fc72d95ae84f75a7abb0e09d4bc577
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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