Diethylamine → HCID 69275117, compound

HRID 272782Notes

Reaction equation

HRID 272782 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH:20]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[C:34]([O:42][CH2:43][CH3:44])[CH:33]=3)[C:21]([N:23]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:24])=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1.C(O)C.CO.C(NCC)C>CCCCCCC>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][C@H:20]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[C:34]([O:42][CH2:43][CH3:44])[CH:33]=3)[C:21]([N:23]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH3:24])=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 18681192Ethanol, mixt. with methanolHCID 69273627HCID 69273627, compound

Product 1

HCID 69275117HCID 69275117, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Example 52 (34 mg) was separated from the racemic mixture (80 mg) of Example 51 using a preparative HPLC equipped with a Chiralpak® AD column (5 cm×50 cm, 20μ). The separations were performed using an isocratic method of 95% 1:1 ethanol/methanol, 5% heptane with 0.1% diethylamine for 120 min with a flow rate of 50 mL/min. Retention time for Example 52 was 26 min. Retention time for the other isomer (32 mg) was 90 min. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.33 (m, 9H) 3.01 (m, 3H) 3.98 (m, 2H) 4.59 (m, 3H) 5.61 (d, J=9.54 Hz, 1H) 6.70 (m, 2H) 7.05 (m, 6H) 7.25 (m, 3H) 7.39 (dd, J=12.96, 6.60 Hz, 1H) 7.95 (m, 1H). LC-MS 499 (M+H).

Workup

  1. customequipped with a Chiralpak® AD column (5 cm×50 cm, 20μ)
  2. customfor 120 min
  3. waitRetention time for the other isomer (32 mg) was 90 min

Sources & evidence

ORD record
ord-e82d804de9d54f66bd5bf7f38a9a4aeb
Source dataset
uspto-grants-2008_11
Patent number
US07456195B2

Reaction notes

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