Water → HCID 67130636, compound

HRID 1746586Notes

Reaction equation

HRID 1746586 reaction equation
O.[NH2:2][C@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.C(=O)([O-])O.[Na+].[C:22]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32](ON2C(=O)CCC2=O)=[O:33])[CH:27]=[CH:28][CH:29]=1)#[N:23]>O1CCOCC1>[C:22]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]([NH:2][C@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)=[O:33])[CH:27]=[CH:28][CH:29]=1)#[N:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6305L-TryptophanHCID 516892Sodium BicarbonateHCID 86655524HCID 86655524, compound

Product 1

HCID 67130636HCID 67130636, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To water (80 mL)-dioxane (80 mL) solution of L-tryptophan (3.0 g) was added sodium hydrogencarbonate (1.3 g) at 0° C., and the mixture was stirred for 30 minutes at room temperature. Next, dioxane (80 mL) solution of the compound obtained in Example 117 (4.2 g) was added to the mixture solution at 0° C., the mixture was stirred for 17 hours at room temperature. The reaction mixture was concentrated to a ⅓ volume under a reduced pressure, thereafter the solution was made acidic with a 10% aqueous citric acid solution, and the crystals precipitated were filtered. The crystals were washed with water, to give the captioned compound (4.6 g, 87%).

Workup

  1. stirringthe mixture was stirred for 17 hours at room temperature
  2. concentrationThe reaction mixture was concentrated to a ⅓ volume under a reduced pressure
  3. customthe crystals precipitated
  4. filtrationwere filtered
  5. washThe crystals were washed with water

Sources & evidence

ORD record
ord-c3bb7f026c2a449bad80eb0a705e72a3
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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