Triethylamine → HCID 178462344, compound

HRID 1424142Notes

Reaction equation

HRID 1424142 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH2:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:13]([NH:20][C@H:21]([C:25](O)=O)[C@@H:22]([CH3:24])[OH:23])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>O1CCOCC1.CCOC(C)=O.C(=O)(O)[O-].[Na+]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]2[NH:11][C:25]([C@@H:21]([NH:20][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[C@H:22]([OH:23])[CH3:24])=[N:12][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 4327084-Tert-butylbenzene-1,2-diamineHCID 2724766N-tert-Butoxycarbonyl-L-threonine

Product 1

HCID 178462344HCID 178462344, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 4-tert-butyl-1,2-diaminobenzene (375 mg, 2.28 mmol) in dioxane (4 mL) was added a solution of N-Boc-L-threonine (500 mg, 2.28 mmol) in dioxane (4 mL) followed by triethylamine (636 μL, 456 mmol) and T3P (1520 mg, 2.40 mmol). The reaction was stirred at room temperature for 10 minutes followed by heating to 100° C. for 18 hours. The reaction was cooled and diluted with EtOAc (50 mL) and saturated aqueous sodium bicarbonate solution (40 mL). The organic layer was collected, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 15-100% TBME in heptanes to afford tert-butyl [(1R,2R)-1-(5-tert-butyl-1H-benzimidazol-2-yl)-2-hydroxypropyl]carbamate.

Workup

  1. temperatureby heating to 100° C. for 18 hours
  2. temperatureThe reaction was cooled
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with 15-100% TBME in heptanes

Sources & evidence

ORD record
ord-daab2d888b994ee099b9780d60d873ae
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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