Hydrochloric Acid → HCID 66750729, compound

HRID 643868Notes

Reaction equation

HRID 643868 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH2:27])=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][NH:27][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:16]=2)[CH:11]=1)[CH3:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 66750577HCID 66750577, compound

Product 1

HCID 66750729HCID 66750729, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3,6-Bis-benzyloxynaphthalen-2-ylamine (0.332 g, 0.934 mmol) is dissolved in DMF (5 mL). Ethyl bromoacetate (0.114 mL, 1.03 mmol) and potassium carbonate (0.194 g, 1.40 mmol) are added. The reaction is heated to 60° C. for 3 h and then poured into 1 N HCl and extracted with EtOAc. The combined organic layers are washed with brine, dried and evaporated to a red foam, which is purified over silica, eluting with 8:1 hexanes/MTBE, to afford (3,6-bis-benzyloxynaphthalen-2-ylamino)-acetic acid ethyl ester as a yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers are washed with brine
  3. customdried
  4. customevaporated to a red foam, which
  5. customis purified over silica
  6. washeluting with 8:1 hexanes/MTBE

Sources & evidence

ORD record
ord-8904dde00250407c94e2dec0cdd95688
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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