Water → Fmoc-N-(2-Boc-aminoethyl)-Gly-OH

HRID 1490089Notes

Reaction equation

HRID 1490089 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C(=O)([O-])O.[Na+].[CH:22]1[C:34]2[CH:33]([CH2:35][O:36][C:37](ON3C(=O)CCC3=O)=[O:38])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][C:13]([OH:15])=[O:14])[C:37]([O:36][CH2:35][CH:33]1[C:32]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:26]2[C:34]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:38])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516892Sodium BicarbonateHCID 9834393({2-[(Tert-butoxycarbonyl)amino]ethyl}amino)acetic acid

Product 1

HCID 2756167Fmoc-N-(2-Boc-aminoethyl)-Gly-OH

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.9 g (50 mmol) of N-(2-tert-butoxycarbonylaminoethyl)aminoacetic acid are stirred together with 50 ml of water, 11.3 g (135 mmol) of sodium hydrogen carbonate and 50 ml of tetrahydrofuran. Subsequently, 24.3 g (72 mmol) of N-(9-fluorenylmethoxycarbonyloxy)succinimide are added. The mixture is stirred at room tmeperature for 20 h and the salt removed by filtration; the filtrate is acidified and the phases separated, and the organic phase is then concentrated.

Workup

  1. customthe salt removed by filtration
  2. customthe phases separated
  3. concentrationthe organic phase is then concentrated

Sources & evidence

ORD record
ord-f821c4dbe7f343db800fbe533e4fffad
Source dataset
uspto-grants-1997_10
Patent number
US05681838

Reaction notes

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