2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 86718854, compound

HRID 1498000Notes

Reaction equation

HRID 1498000 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:20]([NH:22][C@@H:23]([CH2:27][CH2:28][CH2:29][CH3:30])[C:24](O)=[O:25])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][OH:46])=[CH:41][CH:40]=1.C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>C(Cl)Cl>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:17])[NH:18][C@H:19]([C:20](=[O:21])[NH:22][C@H:23]([C:24](=[O:25])[NH:38][C:39]3[CH:44]=[CH:43][C:42]([CH2:45][OH:46])=[CH:41][CH:40]=3)[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 693314-Aminobenzyl alcoholHCID 68281804HCID 68281804, compound

Product 1

HCID 86718854HCID 86718854, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a pear-shaped flask, the above synthesized (S)-2-[(S)-2-(9H-fluoren-9-ylmethoxy-carbonylamino)-3-phenyl-propionylamino]-hexanoic acid (10.72 g, 21 mmol, Eq: 1.00), (4-aminophenyl)methanol (2.717 g, 22 mmol, Eq: 1.03), and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) (7.994 g, 32 mmol, Eq: 1.50) were dissolved in CH2Cl2 (320 ml) and stirred over night under a balloon of Ar. The mixture was poured onto crashed ice/NH4Cl, extracted 2× with AcOEt, washed with H2O, dried over Na2SO4, and the volume reduced to ˜300 ml. The precipitate was filtered off and dryed to give 5.25 g of the title compound as light-brown solid. MS (ISP): (M+H) 606.3.

Workup

  1. additionThe mixture was poured
  2. extractionextracted 2× with AcOEt
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-215701268a4142e096fce5b957338009
Source dataset
uspto-grants-2015_12
Patent number
US09198947B2

Reaction notes

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