Sodium Carbonate → HCID 67186523, compound

HRID 735859Notes

Reaction equation

HRID 735859 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[C:6]([Br:13])[C:3]=1[CH2:4][NH2:5].C([O-])([O-])=O.[Na+].[Na+].[C:20](ON1C(=O)CCC1=O)([O:22][CH2:23][CH:24]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21]>O1CCOCC1>[C:20]([NH:5][CH2:4][C:3]1[C:2]([Br:1])=[CH:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=1[Br:13])([O:22][CH2:23][CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[C:36]1=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:21]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 67188193HCID 67188193, compound

Product 1

HCID 67186523HCID 67186523, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,6-dibromo-4-carboxybenzylamine (20 g, 0.064 mol) in dioxane (500 mL), was added an aqueous solution of Na2CO3 (10%, 410 mL) with stirring. After stirring at 26° C. for 15 min was added Fmoc-OSu (30.5 g, 0.09 mol) in portions for 2 h and allowed to stir at ambient temperature for 24 h. The solid precipitate was filtered off and washed with diethyl ether (3×200 mL), followed by methanol (3×200 mL). The solid salt was acidified with an aqueous solution of HCl (3 N, 100 mL) to pH=2. The precipitate was filtered under suction and dried. The crude solid was recrystalised from methanol/diethyl ether to give N-(Fmoc)-2,6-dibromo-4-carboxybenzylamine (30 g, 87%) as a solid.

Workup

  1. stirringAfter stirring at 26° C. for 15 min
  2. stirringto stir at ambient temperature for 24 h
  3. filtrationThe solid precipitate was filtered off
  4. washwashed with diethyl ether (3×200 mL)
  5. filtrationThe precipitate was filtered under suction
  6. customdried
  7. customThe crude solid was recrystalised from methanol/diethyl ether

Sources & evidence

ORD record
ord-17941ce9ec2f4c79b88cf59ad93cb716
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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