Triethylamine → HCID 86699912, compound

HRID 530473Notes

Reaction equation

HRID 530473 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:24][C@@H:25]([C:29]([OH:31])=[O:30])[C@H:26]([CH3:28])[OH:27].CCN(CC)CC>CN(C=O)C.O>[OH:27][C@@H:26]([CH3:28])[C@@H:25]([NH:24][C:6]([O:23][CH2:22][CH2:21][CH2:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])[C:29]([OH:31])=[O:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 69435D-ThreonineHCID 76889Benzenebutanol

Product 1

HCID 86699912HCID 86699912, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

In a four necked round bottom flask, CDI (10.6 g, 65.5 mmol) was added to a solution of 4-phenylbutan-1-ol (5 mL, 32.8 mmol) in anhydrous DMF (70 mL) under argon. After stirring 2 h at rt, D-threonine (3.90 g, 32.8 mmol) dissolved in water (70 mL) and Et3N (6.8 mL, 49.1 mmol) were added. The mixture was heated at 50° C. for 16 h then allowed to cool. Water (700 mL) was added and the mixture washed with Et2O (3×300 mL). The aqueous phase was acidified with 2M HCl solution then extracted with AcOEt (3×500 mL). The collected organic phases were dried over Na2SO4, filtered and the solvent removed under vacuum. The crude was further co-evaporated with toluene to give a pale yellow oil (5.2 g, 54%), which was used in the next step without further purification. MS (ESI) m/z: 296[M+H]+; 294[M−H]−. Rf=0.34 (Cy/AcOEt 2:8+1% CH3COOH). FTIR (cm−1): 3332 (br), 3027, 2978, 2938, 2863, 1719 (br), 1525, 1253, 1069, 779, 748, 699.

Workup

  1. temperatureThe mixture was heated at 50° C. for 16 h
  2. temperatureto cool
  3. washthe mixture washed with Et2O (3×300 mL)
  4. extractionthen extracted with AcOEt (3×500 mL)
  5. dry with materialThe collected organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-d2033334ac374aa6bb0926e3c195ef2d
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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