Diisopropylethylamine → HCID 23378496, compound

HRID 1280079Notes

Reaction equation

HRID 1280079 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=O)=[CH:5][CH:4]=1)=[O:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:45][CH2:46][CH2:47][NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52]>C(Cl)Cl.CCOC(C)=O>[C:51]([O:50][C:49](=[O:55])[NH:48][CH2:47][CH2:46][NH:45][C:9](=[O:11])[CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:13][CH:12]=1)([CH3:54])([CH3:52])[CH3:53]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 89177Acetic acid, 2-(4-formylphenoxy)-HCID 187201N-BOC-ethylenediamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 23378496HCID 23378496, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Formylphenoxyacetic acid (0.306 g, 1.70 mmol) was dissolved in DCM (5 mL). DIEA (0.524 g, 4 mmol) and TBTU (0.550 g, 1.70 mmol) were added followed by tert-butyl N-(2-aminoethyl)carbamate (0.250 g, 1.56 mmol). The mixture was stirred 2 h at room temperature, dissolved in EtOAc and washed sequentially with 5% aqueous K2CO3, KHSO4, water and brine. The extract was dried (MgSO4) and concentrated under reduced pressure to give a yellow solid (0.350 g).

Workup

  1. washwashed sequentially with 5% aqueous K2CO3, KHSO4, water and brine
  2. dry with materialThe extract was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37404b6af83f4ec9abb5cc832c699e8b
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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