Sodium Carbonate → 578026-61-6

HRID 735857Notes

Reaction equation

HRID 735857 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].C([O-])([O-])=O.[Na+].[Na+].[C:19](ON1C(=O)CCC1=O)([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20]>O1CCOCC1>[C:19]([NH:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:2]=1[Br:1])([O:21][CH2:22][CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[C:35]1=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 67186377HCID 67186377, compound

Product 1

HCID 67188028578026-61-6Yield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 2-bromo-4-carboxybenzylamine (20 g, 0.086 mol) in dioxane (250 mL), was added an aqueous solution of Na2CO3 (10%, 350 mL) with stirring. The reaction mixture was cooled to 10° C., added Fmoc-OSu (32 g, 0.096 mol) in portions and allowed to stir at RT for 8 h. The solid precipitate was filtered off and washed with diethyl ether (2×200 mL). The solid was acidified with 3N HCl and filtered under suction. The crude solid was recrystalised from methanol/diethyl ether to give N-(Fmoc)-2-bromo-4-carboxybenzylamine (26 g, 67%) as a solid.

Workup

  1. stirringto stir at RT for 8 h
  2. filtrationThe solid precipitate was filtered off
  3. washwashed with diethyl ether (2×200 mL)
  4. filtrationfiltered under suction
  5. customThe crude solid was recrystalised from methanol/diethyl ether

Sources & evidence

ORD record
ord-a69768e62e2246d4ab6f9229ad84b207
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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