N-(indole-3-acetyl)-L-leucine → 2-(2-1H-Indol-3-ylacetylamino)-4-methylpentanoic acid (4-dimethylamino-4-phenylcyclohexyl)amide

HRID 1394248Notes

Reaction equation

HRID 1394248 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([NH2:9])[CH2:5][CH2:4]1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[NH:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]([CH2:44][C:45]([NH:47][C@H:48]([C:53](O)=[O:54])[CH2:49][CH:50]([CH3:52])[CH3:51])=[O:46])=[CH:36]1>CO>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([NH:9][C:53](=[O:54])[CH:48]([NH:47][C:45](=[O:46])[CH2:44][C:37]2[C:38]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[NH:35][CH:36]=2)[CH2:49][CH:50]([CH3:52])[CH3:51])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 688142N-(indole-3-acetyl)-L-leucineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 129862564-Dimethylamino-4-phenyl-cyclohexylamine

Product 1

HCID 98282222-(2-1H-Indol-3-ylacetylamino)-4-methylpentanoic acid (4-dimethylamino-4-phenylcyclohexyl)amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The more polar diastereomer of (4-dimethylamino-4-phenyl-cyclohexyl)amine (143 mg, 0.66 mmole) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (272 mg, 0.98 mmole) were added to a solution of N-(3-indolylacetyl)-L-leucine (189 mg, 0.66 mmole) in MeOH and stirred for 24 h at room temperature. Working up was performed by removing MeOH by distillation. The residue was re-dissolved with water, adjusted to pH 11 with 5M NaOH and extracted with ethyl acetate. The organic phase was dried with Na2SO4 and then evaporated. The product was obtained as a colorless oil in a yield of 320 mg (100%).

Workup

  1. customby removing MeOH
  2. distillationby distillation
  3. dissolutionThe residue was re-dissolved with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried with Na2SO4
  6. customevaporated
  7. customThe product was obtained as a colorless oil in a yield of 320 mg (100%)

Sources & evidence

ORD record
ord-703888c173c54a6e9d6716b16927691b
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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