1,2-Dichloroethane → HCID 86633507, compound

HRID 1173155Notes

Reaction equation

HRID 1173155 reaction equation
C(OC([N:8]1[CH2:20][CH2:19][C:11]2([O:15][N:14]=[C:13]([C:16](O)=[O:17])[CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)CCl.C1C=CC2N(O)N=[N:31]C=2C=1.C(N)CC1C=CC=CC=1>CN(C=O)C.CCOC(C)=O>[O:15]1[C:11]2([CH2:19][CH2:20][NH:8][CH2:9][CH2:10]2)[CH2:12][C:13]([C:16]([NH2:31])=[O:17])=[N:14]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1001PhenethylamineHCID 757711-HydroxybenzotriazoleHCID 114149018-(tert-Butoxycarbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid

Product 1

HCID 86633507HCID 86633507, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-(tert-butoxycarbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid (300 mg, 1.06 mmol), EDC (242 mg, 1.26 mmol), HOBt (171 mg, 1.26 mmol) in DMF (4 mL) was added phenethylamine (159 μL, 1.26 mmol). After 4 h at room temperature, the reaction mixture was diluted with EtOAc (10 mL) and washed with H2O (1×5 mL) and brine (1×5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The crude oil was taken up in CH2Cl2 (4 mL) and treated with TFA (2 mL). The reaction mixture was concentrated and the crude oil purified by reverse-phase chromatography (10-75% MeCN/H2O with 0.05% TFA) to give the N2-phenylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide confirmed by MS (ESI+): cal'd [M+H]+ 288.2, obs'd 288.2.

Workup

  1. washwashed with H2O (1×5 mL) and brine (1×5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additiontreated with TFA (2 mL)
  6. concentrationThe reaction mixture was concentrated
  7. customthe crude oil purified by reverse-phase chromatography (10-75% MeCN/H2O with 0.05% TFA)

Sources & evidence

ORD record
ord-c6c02b0930104558b45960e4df65f0b3
Source dataset
uspto-grants-2010_11
Patent number
US07834026B2

Reaction notes

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