Diisopropylethylamine → HCID 10030465, compound

HRID 2184669Notes

Reaction equation

HRID 2184669 reaction equation
[CH2:1]([C@@H:5]1[NH:11][C@H:10]([CH3:12])[CH2:9][CH2:8][N:7]([C@@H:13]([CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[C:14]([NH2:16])=[O:15])[C:6]1=[O:28])[CH:2]([CH3:4])[CH3:3].[N:29]1[C:38]2[C:33](=[CH:34][C:35]([CH2:39][C:40](O)=[O:41])=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:1]([C@@H:5]1[N:11]([C:40](=[O:41])[CH2:39][C:35]2[CH:34]=[C:33]3[C:38](=[CH:37][CH:36]=2)[N:29]=[CH:30][CH:31]=[CH:32]3)[C@H:10]([CH3:12])[CH2:9][CH2:8][N:7]([C@@H:13]([CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[C:14]([NH2:16])=[O:15])[C:6]1=[O:28])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 117887092-(Quinolin-6-yl)acetic acidHCID 12012105HCID 12012105, compound

Product 1

HCID 10030465HCID 10030465, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-[(3S,5R)-3-isobutyl-5-methyl-2-oxo-[1,4]diazepan-1-yl]-3-(naphthalen-2-yl)-propionamide (382 mg, 1 mmol) is added to a solution of 6-quinolylacetic acid (372 mg, 2 mmol), Hünig's base (170 μl, 1 mmol) and EADC (383 mg, 2 mmol) in CH2Cl2 (50 ml). After 16 hours at RT the reaction mixture is extracted with 0.1 N HCl and then with 5% NaHCO3 solution. Pure title compound is isolated after silica gel chromatography using ethyl acetate —>ethyl acetate/MeOH (9/1) as mobile phase. MH+:551.4 (ESI) αD20=−12.5° (c=0.12 95% AcOH)

Workup

  1. extractionAfter 16 hours at RT the reaction mixture is extracted with 0.1 N HCl

Sources & evidence

ORD record
ord-4402a4cca7fd4c17889f2c4d4ca59636
Source dataset
uspto-grants-2002_06
Patent number
US06399599B1

Reaction notes

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