Triethylamine → HCID 118276670, compound

HRID 1053662Notes

Reaction equation

HRID 1053662 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([O:12]N1C(=O)CCC1=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:28][CH2:29][CH2:30][N:31]([CH2:40][CH2:41][Cl:42])[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([NH2:39])[CH:33]=1.C(N(CC)CC)C>C(#N)C>[Cl:28][CH2:29][CH2:30][N:31]([CH2:40][CH2:41][Cl:42])[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([NH:39][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13178396Boc-Asp(OtBu)-OSuHCID 118276667HCID 118276667, compound

Product 1

HCID 118276670HCID 118276670, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Adapting a literature known protocol (Levi and Weed, U.S. Pat. No. 3,235,594 (1966)), to a solution of O1-(2,5-Dioxopyrrolidin-1-yl)O4-tert-butyl(2S)-2-(tert-butoxycarbonylamino)-butanedioate (Boc-L-Asp(Osu)-OtBu) (6a) (386 mg, 1.0 mmol) in anhydrous acetonitrile (MeCN) (10 mL) is added N,N-bis(2-chloroethyl)-4-methyl-benzene-1,3-diamine (16b) as a bis hydrochloride salt (320 mg, 1.0 mmol) followed by neat triethylamine (Et3N, TEA) (321 μL, 233 mg, 2.3 mmol). The reaction mixture is stirred for about 12 h at room temperature. The reaction is followed by TLC and/or LC/MS to completion. The volatile solvents are removed under reduced pressure using a rotary evaporator. Aqueous work-up and purification by silica gel column chromatography furnish the target compound (16c).

Workup

  1. customThe volatile solvents are removed under reduced pressure
  2. customa rotary evaporator
  3. customAqueous work-up and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-bce8648fd41e45c5a1f4715429f41b4f
Source dataset
uspto-grants-2016_07
Patent number
US09394237B2

Reaction notes

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