Hydrochloric Acid → HCID 22961864, compound

HRID 365931Notes

Reaction equation

HRID 365931 reaction equation
C([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([Cl:29])=[C:18]([CH2:20][NH:21][C:22]([C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH:19]=1)(OC(C)(C)C)=O.Cl.Cl.CCOCC.CO>O>[ClH:29].[NH:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([Cl:29])=[C:18]([CH2:20][NH:21][C:22]([C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 10953452Ether hydrochlorideHCID 22961824HCID 22961824, compound

Product 1

HCID 22961864HCID 22961864, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product of step 213a (0.20 g, 0.50 mmol) was deprotected and isolated as the free base in 64% yield according to the procedure of Example 20b, followed by conversion to the hydrochloride with HCl/Et2O. [α]D23 +21.67 (c 0.7, MeOH); 1H NMR (D2O, 300 MHz) δ 2.66 (dd, J=8.5, 16.5 Hz, 2H), 4.02-4.17 (m, 2H), 4.42 (d, J=4.0 Hz, 2H), 4.64 (s, 2H), 4.88 (m, 1H), 6.68 (dd, J=1.5, 5.5 Hz, 1H), 7.23 (dd, J=1.0, 3.5 Hz, 1H), 7.52 (d, J=3.0 Hz, 1H), 7.72 (d, J=1.5 Hz, 1H), 8.11 (d, J=2.5 Hz, 1H); MS (CI/NH3) m/z 322 (M+H)+. Anal. Calcd for C15H16ClN3O3.1.2 HCl.0.2 H2O: C, 48.81; H, 4.81; N, 11.38. Found: C, 48.70; H, 4.76; N, 11.03.

Workup

  1. customisolated as the free base in 64% yield

Sources & evidence

ORD record
ord-37b5a65a1c3844e3a8455afa60b16a76
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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