tert-Butyl carbazate → HCID 68697521, compound

HRID 1157673Notes

Reaction equation

HRID 1157673 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12](O)=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C(N(CC)C(C)C)(C)C.CN([C:31]([O:35]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:50]([O:54][C:55](=[O:58])[NH:56][NH2:57])([CH3:53])([CH3:52])[CH3:51]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([N:10]2[CH2:17][CH2:16][CH2:15][CH:11]2[CH2:12][C:31]([NH:57][NH:56][C:55]([O:54][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:58])=[O:35])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 4

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68699150HCID 68699150, compound

Product 1

HCID 68697521HCID 68697521, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-(3-chloro-4-cyano-2-methylphenyl)proline (0.623 g, 2.350 mmol), N,N-diisopropylethylamine (1.420 g, 11.750 mmol) and TBTU (1.113 g, 3.530 mmol) in DMF add a solution of t-butlycarbazate (0.462 g, 3.530 mmols) in DMF. Leave to stand for 3 h, then partition between ethyl acetate and 10% (w/w) aqueous citric acid. Extract the organic with 2N aqueous sodium hydroxide solution, then brine. Dry over magnesium sulphate, filter, and concentrate under reduced pressure to obtain the title compound. (0.89 g, 100%) mass spectrum (m/e): 379 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.80 (s, 1H), 7.42 (d, 1H), 6.38 (d, 1H), 6.22 (bs, 1H) 4.33 (t, 1H), 3.88 (m, 1H), 3.04 (m, 1H), 2.81 (m, 3H), 2.53 (m, 1H), 1.85-2.38 (m. 3H), 1.41 (s, 9H).

Workup

  1. customLeave
  2. custompartition between ethyl acetate and 10% (w/w) aqueous citric acid
  3. extractionExtract the organic with 2N aqueous sodium hydroxide solution
  4. dry with materialDry over magnesium sulphate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-bf42d41949c941498c68877d915dd5cd
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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