Triethylamine → HCID 86704313, compound

HRID 78734Notes

Reaction equation

HRID 78734 reaction equation
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CCOC(C)=O.[CH3:25][C:26]([O:29][C:30]([NH:32][C@@H:33]([CH2:39][CH3:40])/[CH:34]=[CH:35]/[C:36]([OH:38])=O)=[O:31])([CH3:28])[CH3:27].[NH:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43][CH2:42]1.CCN(CC)CC>C(Cl)Cl>[N:41]1([C:36](=[O:38])/[CH:35]=[CH:34]/[C@@H:33]([NH:32][C:30](=[O:31])[O:29][C:26]([CH3:25])([CH3:27])[CH3:28])[CH2:39][CH3:40])[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43][CH2:42]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10328IndolineHCID 111923Propylphosphonic anhydrideHCID 86704312(2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-hexenoic acid

Product 1

HCID 86704313HCID 86704313, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 50 wt % ®T3P in EtOAc (22.00 mL, 37.0 mmol) was added dropwise via addition funnel to a solution of (2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}-amino)-2-hexenoic acid (5.65 g, 24.64 mmol), 2,3-dihydro-1H-indole (2.76 mL, 24.64 mmol), and Et3N (11 mL, 79 mmol) in CH2Cl2 (90 mL) at 0° C. (bath temp). The ice bath was removed, and the reaction was stirred at RT. After 30 min, the reaction was quenched by dropwise addition of saturated aq. NaHCO3 (50 mL). The layers were separated, and the reaction was washed with 10% citric acid (1×50 mL). The organic layer was concentrated under a stream of nitrogen, and the residue was purified by flash column chromatography, giving 7.21 g (89%) of the title compound. LC-MS m/z 331 (M+H)+, 1.05 (ret time).

Workup

  1. customThe ice bath was removed
  2. customthe reaction was quenched by dropwise addition of saturated aq. NaHCO3 (50 mL)
  3. customThe layers were separated
  4. washthe reaction was washed with 10% citric acid (1×50 mL)
  5. concentrationThe organic layer was concentrated under a stream of nitrogen
  6. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-0979e192fad94202b22a5e2006d53b1e
Source dataset
uspto-grants-2014_09
Patent number
US08841463B2

Reaction notes

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