4-Methylmorpholine → HCID 15631179, compound

HRID 1761419Notes

Reaction equation

HRID 1761419 reaction equation
[N+:1]([C:4]1[C:5]([S:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([NH:20][C@@H:21]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:22][CH2:23][C:24]([N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][C@H:27]2[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:25])=[O:19])[NH2:17])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CN1CCOCC1.[CH2:52]1[O:72][C:71]2[CH:70]=[CH:69][C:56]([CH2:57][O:58][C:59](ON3C(=O)CCC3=O)=[O:60])=[CH:55][C:54]=2[O:53]1>C(Cl)Cl>[CH2:52]1[O:72][C:71]2[CH:70]=[CH:69][C:56]([CH2:57][O:58][C:59]([NH:17][C@H:16]([C:18]([NH:20][C@@H:21]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:22][CH2:23][C:24]([N:26]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:28][C@H:27]3[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:25])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12][NH:11][S:10][C:5]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=3)=[O:60])=[CH:55][C:54]=2[O:53]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 15631177HCID 15631177, compoundHCID 20044066HCID 20044066, compound

Product 1

HCID 15631179HCID 15631179, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An aliquot (1.0 g) of the resulting ester was dissolved in 30 ml of methylene chloride, and 0.21 g of N-methylmorpholine and 1.07 g of N-(3,4-methylenedioxybenzyloxycarbonyloxy)succinimide were added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed successively with saturated aqueous sodium bicarbonate solution, 5% aqueous potassium hydrogensulfate solution, and water, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The residue was recrystallized from ethanol/methanol to give 1.1 g of ethyl 1-[N2 -(3,4-methylenedioxybenzyloxycarbonyl)-N6 -(3-nitro-2-pyridinesulfenyl)-L-lysyl-O1 -ethyl-gamma-D-glutamyl]indoline-2(S)-carboxylate. mp. 130°-135° C. [α]D27 : -23.2° (dimethylformamide).

Workup

  1. washThe reaction mixture was washed successively with saturated aqueous sodium bicarbonate solution, 5% aqueous potassium hydrogensulfate solution, and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue was recrystallized from ethanol/methanol

Sources & evidence

ORD record
ord-2bd6ef677c4c4d8aa1c586314123f291
Source dataset
uspto-grants-1989_05
Patent number
US04826814

Reaction notes

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