1,2-Dichloroethane → HCID 24744642, compound

HRID 2360550Notes

Reaction equation

HRID 2360550 reaction equation
C(O[C:6]([N:8]1[CH2:20][CH2:19][C:11]2([O:15][N:14]=[C:13]([C:16]([OH:18])=O)[CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH2:21](Cl)[CH2:22]Cl.[CH:25]1[CH:26]=[CH:27][C:28]2[N:33](O)N=[N:31][C:29]=2[CH:30]=1.[CH2:35]([NH2:43])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CN([CH:47]=[O:48])C>CCOC(C)=O>[NH2:33][C:28]1[CH:27]=[CH:26][C:25]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:30][C:29]=1[NH:31][C:47]([C:36]1[CH:21]=[CH:22][C:6]([N:8]2[CH2:9][CH2:10][C:11]3([O:15][N:14]=[C:13]([C:16]([NH:43][CH2:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:18])[CH2:12]3)[CH2:19][CH2:20]2)=[N:43][CH:35]=1)=[O:48]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 1001PhenethylamineHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 114149018-(tert-Butoxycarbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid

Product 1

HCID 24744642HCID 24744642, compound

Reagents, catalysts & solvents 1

HCID 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 mL, 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 N-(2-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-0642eabaef1f4a1b9bb0c792db526afb
Source dataset
uspto-grants-2014_04
Patent number
US08686020B2

Reaction notes

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