Water → Benzyl 5-(tert-butyloxycarbonylamino)indole-2-carboxylate

HRID 1455898Notes

Reaction equation

HRID 1455898 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([OH:20])=[O:19])=[CH:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([O:20][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:19])=[CH:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 158871475-(((tert-butoxy)carbonyl)amino)-1H-indole-2-carboxylic acid

Product 1

HCID 22105409Benzyl 5-(tert-butyloxycarbonylamino)indole-2-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 31 (2.03 g, 7.4 mmol) in DMF (50 mL) was treated with sodium bicarbonate (1.8 g, 21.4 mmol), and benzyl bromide (4 mL, 33.6 mmol). The reaction mixture was stirred for 18 h at room temperature. Water (50 mL) was added and the product was extracted with ethyl acetate (80 mL×3). The solution was dried with sodium sulfate, concentrated in vacuo to give compound 32 (2.27 g, 84% yield) as a white solid. m.p.180°-182° C. 1H NMR (DMSO-d6, ppm): 11.93 (s, 1 H, NH), 7.51-7.02 (m, 9 H, Ar--H), 5.38 (s, 2 H, CH2C6 H5), 1,48 (s, 9 H, C(CH3)3). Anal. (C21H22 N2O4 0.25H2O), C, H, N.

Workup

  1. extractionthe product was extracted with ethyl acetate (80 mL×3)
  2. dry with materialThe solution was dried with sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b5a4e2f74584964b63466994ddee434
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

Loading…