Diisopropylethylamine → HCID 59400104, compound

HRID 2389537Notes

Reaction equation

HRID 2389537 reaction equation
Cl.Cl.[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]([NH2:13])[CH2:4]1.C(N(C(C)C)CC)(C)C.[C:23]([OH:33])(=[O:32])[C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C1C=CN=CC=1.CN(C)C=O.C(OCC)(=O)C>[OH:25][C@@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23]([NH:13][C@@H:5]1[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:3][CH2:4]1)=[O:32].[OH:25][C@@H:24]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:23]([NH:13][C@H:5]1[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:3][CH2:4]1)=[O:33]

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 439616(S)-mandelic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 42614143HCID 42614143, compound

Product 2

HCID 59400104HCID 59400104, compoundHCID 59400306HCID 59400306, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,2,3,4-tetrahydroquinolin-3-amine bis HCl salt (925 mg), diisopropylethylamine (4 mL), L-(+)mandelic acid (636 mg) and 4-dimethylaminopyridine (510 mg) in dimethylformamide (40 mL) was added HBTU (1.6 g). The mixture was stirred at room temperature for 48 hours before being poured into ethyl acetate (150 mL), washed with water (2×400 mL), dried over magnesium sulfate and evaporated to dryness. The crude product was purified by flash chromatography using a gradient (50-70% ethyl acetate in hexanes) to give (S)-2-hydroxy-2-phenyl-N—((R)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (310 mg) and (S)-2-hydroxy-2-phenyl-N—((S)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (360 mg) as white solids. 1H NMR (DMSO-d6) 400 MHz δ 7.79 (d, J=8 Hz, 1H), 7.41-7.25 (m, 5H), 6.91-6.85 (m, 2H), 6.51-6.45 (m, 2H), 6.25 (d, J=4.4 Hz, 1H), 5.76 (br s, 1H), 4.90 (d, J=5.2 Hz, 1H), 4.09-4.01 (m, 1H), 3.18-3.14 (m, 1H), 3.03-2.98 (m, 1H), 2.87-2.81 (m, 1H), 2.76-2.70 (m, 1H). LCMS m/e 283 (M+H).

Workup

  1. washwashed with water (2×400 mL)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c25330f50b174b98b89795233980c6c2
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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