Triethylamine → HCID 53814266, compound

HRID 2186501Notes

Reaction equation

HRID 2186501 reaction equation
[N:1]([CH2:4][C@H:5]([OH:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N+:2]=[N-:3].C(N([CH2:18][CH3:19])CC)C>CN(C)C1C=CN=CC=1.O1CCCC1>[N:1]([CH2:4][C@H:5]([O:12][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:18][CH3:19])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 11789689HCID 11789689, compound

Product 1

HCID 53814266HCID 53814266, compoundYield 186.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 100 ml four-necked flask were charged 6.0 g (34.6 mmol) of ethyl (R)-4-azido-3-hydroxybutyrate, 4.2 g (41.5 mmol) of triethylamine, 0.12 g (1.04 mmol) of 4-dimethylaminopyridine, and 60 ml of tetrahydrofuran and the mixture was cooled to 0° C. 5.10 g (38.1 mmol) of hexanoyl chlrodie was slowly added thereto dropwise in a nitrogen stream. After the addition, the reaction mixture was stirred at a room temperature for 5 hours, and then 14 ml of 5% HCL was added thereto. After the liquid separation, the mixture was washed thrice with 30 ml of 5% aqueous solution of sodium chloride and then concentrated to give 8.75 g (93%) of the title compound.

Workup

  1. addition5.10 g (38.1 mmol) of hexanoyl chlrodie was slowly added
  2. additionAfter the addition
  3. addition14 ml of 5% HCL was added
  4. customAfter the liquid separation
  5. washthe mixture was washed thrice with 30 ml of 5% aqueous solution of sodium chloride
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0dd98e22cc5b4981b43588aa132e38a6
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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