Dimethylformamide → HCID 86627959, compound

HRID 251732Notes

Reaction equation

HRID 251732 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=N[CH2:27][CH2:28][CH2:29][N:30](C)C.Cl.[CH:34]1[CH:35]=[CH:36][C:37]2N(O)N=N[C:38]=2[CH:39]=1.CCN([CH:50]([CH3:52])[CH3:51])C(C)C.CN(C=[O:57])C>>[O:57]=[C:28]([C:27]1[CH:51]=[CH:50][C:52]2[C:35](=[CH:34][CH:39]=[CH:38][CH:37]=2)[CH:36]=1)[CH2:29][NH:30][C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])=[O:12]

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11197378HCID 11197378, compound

Product 1

HCID 86627959HCID 86627959, compound

Procedure

A solution of (2S)-2-[(tert-butoxycarbonyl)amino]-8-oxodecanoic acid, EDC.HCl (1.3 eq.) and HOBt (1.3 eq.) in DMF was shaken for 5 min. To the mixture was added a solution of crude amine (L2) (1 eq.) and DIPEA (1 eq.) in DMF. The mixture was left to stir for 1 h. It was partitioned between DMF and 1 M NaOH. The DCM phase was washed sequentially with 1 M NaOH, 1 M HCl and brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by chromatography on silica using 50% EtOAc/Petroleum ether as eluent to yield the product was obtained as a colourless oil. MS (ES) C27H36N2O5 requires: 468, found: 469 (M+H)+.

Workup

  1. waitThe mixture was left
  2. customIt was partitioned between DMF and 1 M NaOH
  3. washThe DCM phase was washed sequentially with 1 M NaOH, 1 M HCl and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica using 50% EtOAc/Petroleum ether as eluent
  7. customto yield the product
  8. customwas obtained as a colourless oil

Sources & evidence

ORD record
ord-95afda6f70f14f148df99da76ff06de6
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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