N-BOC-ethylenediamine → HCID 21480554, compound

HRID 356800Notes

Reaction equation

HRID 356800 reaction equation
[C:1](=O)([O:17]N1C(=O)CCC1=O)[O:2][CH2:3][C:4]1[C:16]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1.[C:26]([O:30][C:31]([NH:33][CH2:34][CH2:35][NH2:36])=[O:32])([CH3:29])([CH3:28])[CH3:27]>C(#N)C.C([O-])([O-])=O.[Na+].[Na+]>[C:26]([O:30][C:31]([NH:33][CH2:34][CH2:35][NH:36][C:1]([O:2][CH2:3][C:4]1[C:16]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:17])=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 18704421HCID 18704421, compound

Product 1

HCID 21480554HCID 21480554, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of fluorenylmethyl succinimidyl carbonate (31.0 g, 0.092 mol) in acetonitrile (300.0 ml) was slowly added to mono tert-butyloxycarbonylethylenediamine (10.0 g, 0.063 mol) dissolved in 10% aq. Na2CO3 (250 ml). Acetonitrile was evaporated and the product was extracted with ethyl acetate, organic phase was dried over Na2CO3, concentrated and the product was allowed to crystallize by adding petroleum ether. The product was collected on filter, washed with petroleum ether. Yield 20.0 g (84%). TLC petroleum ether--diethylether 88:12 Rf 0.64. NMR (300 MHz, DMSO-d6, 25° C.) d: 1.37 (s, 9H, tBu), 2.99 (m, 4H, CH2CH2), 4.20-4.29 (m, 3H, Fmoc OCH2CH--), 6.76 (t, 1H, NH), 7.25 (t, 1H, NH), 7.33-7.89 (m, 8H, Fmoc). M.p. 146°-148° C.

Workup

  1. customAcetonitrile was evaporated
  2. extractionthe product was extracted with ethyl acetate, organic phase
  3. dry with materialwas dried over Na2CO3
  4. concentrationconcentrated
  5. customto crystallize
  6. additionby adding petroleum ether
  7. customThe product was collected
  8. filtrationon filter
  9. washwashed with petroleum ether

Sources & evidence

ORD record
ord-e87775f86c174dd69809cc5ee5ce9934
Source dataset
uspto-grants-1998_11
Patent number
US05840485

Reaction notes

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