Triethylamine → {4-[4-(Benzyloxycarbonylamino)phenoxy]pyridin-2-yl}-N-(phenoxycarbonyl)carbamic acid phenyl ester

HRID 2265608Notes

Reaction equation

HRID 2265608 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:31][CH3:32])CC)C.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35]>O1CCCC1>[C:37]1([O:36][C:34](=[O:35])[N:24]([C:20]2[CH:19]=[C:18]([O:17][C:14]3[CH:15]=[CH:16][C:11]([NH:10][C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:25])=[CH:12][CH:13]=3)[CH:23]=[CH:22][N:21]=2)[C:9]([O:25][C:32]2[CH:31]=[CH:4][CH:3]=[CH:2][CH:1]=2)=[O:8])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 59596944[4-(2-Aminopyridin-4-yloxy)phenyl]carbamic acid benzyl ester

Product 1

HCID 59596983{4-[4-(Benzyloxycarbonylamino)phenoxy]pyridin-2-yl}-N-(phenoxycarbonyl)carbamic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(2-aminopyridin-4-yloxy)phenyl]carbamic acid benzyl ester (500 mg) in tetrahydrofuran (15 ml) were added triethylamine (0.519 ml) and phenyl chloroformate (0.467 ml) while stirring in an ice water bath. The reaction mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned between ethyl acetate (50 ml) and a saturated aqueous solution of sodium hydrogencarbonate (20 ml). The separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml) in this order, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to provide a crude product of the titled compound as brown foam (935.6 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 min
  2. customThe reaction mixture was partitioned between ethyl acetate (50 ml)
  3. washThe separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml) in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9815280601f54d11a07505a089c5c650
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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