Diisopropylethylamine → HCID 59505283, compound

HRID 1253644Notes

Reaction equation

HRID 1253644 reaction equation
C(N(C(C)C)C(C)C)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([C:22]([OH:24])=O)[CH:16]=[CH:15]2.O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:37][O:38][C:39]([C:41]1[CH:42]=[C:43]2[C:47](=[CH:48][CH:49]=1)[CH2:46][CH2:45][C@H:44]2[NH2:50])=[O:40]>C(Cl)Cl.C(OCC)(=O)C>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([C:22]([NH:50][C@H:44]1[C:43]3[C:47](=[CH:48][CH:49]=[C:41]([C:39]([O:38][CH3:37])=[O:40])[CH:42]=3)[CH2:46][CH2:45]1)=[O:24])[CH:16]=[CH:15]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 3491816-Methoxy-2-Naphthoic AcidHCID 27960291-Hydroxybenzotriazole hydrateHCID 66700566(R)-methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate hydrochloride

Product 1

HCID 59505283HCID 59505283, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-Ethyl-diisopropylamine (3 eq.) was added to an ice-cold solution of 6-methoxy-2-naphthoic acid (1 eq.) in methylene chloride. The reaction mixture was cooled to 0° C. and N-ethyl-N′-3-(dimethylamino)-propyl-carbodiimide hydrochloride (1.2 eq.) and 1-hydroxybenzotriazole hydrate (0.2 eq.) were then added. The mixture was stirred at this temperature for 15 min, before (3R)-3-amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-03 HCl) (0.989 mmol, 1 eq.) was added. The reaction mixture was then stirred at room temperature overnight. The mixture was diluted with ethyl acetate and the organic phase was washed with 10% NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica, cyclohexane/ethyl acetate 2:1) to obtain the desired compound (B-10). Yield: 83%

Workup

  1. additionwas added
  2. washthe organic phase was washed with 10% NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica, cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-b99d65b59f534dbc81f7e36464b95255
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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