Water → HCID 59752882, compound

HRID 1909760Notes

Reaction equation

HRID 1909760 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][C@@H:8]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[CH:30][CH:29]=[N:28]3)=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.O>Cl>[N:27]1([C:24]2[CH:23]=[CH:22][C:21]([O:20][C:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:12][C@H:8]4[CH2:9][CH2:10][CH2:11][N:7]4[CH2:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[CH:15][CH:16]=3)=[CH:26][CH:25]=2)[CH:31]=[CH:30][CH:29]=[N:28]1

Participants

4

Reactant 2

HCID 962WaterHCID 68996845HCID 68996845, compound

Product 1

HCID 59752882HCID 59752882, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a 20 mL vial which contained a solution of the product from step 1 (40 mg, 0.1 mmol) in HCl (4 N in dioxane 2 mL) was added water (0.3 mL) at 0° C. The mixture was allowed to warm to rt and stir at rt for 24 h. The solvent was removed to yield the crude, which was purified by recrystallization from THF-ether to afford the title product (25 mg, 75%); LCMS; 94%, ESI−, Calcd: 421.5; Found m/z: 420.6 (M−1); 1H NMR (400 MHz, DMSO-d6); δ 1.74-2.09 (m, 5H), 2.16-2.25 (m, 1H), 2.31-2.40 (m, 2H), 3.03 (br, 2H), 3.45-3.80 (m, 3H), 4.16-4.20 (m, 1H), 4.20-4.23 (m, 1H), 6.52 (t, J=2.0 Hz, 1H), 6.87 (s, 1H), 7.04-7.06 (m, 5H), 7.71 (d, J=1.6 Hz, 1H), 7.80 (d, J=9.2 Hz, 2H), 8.42 (d, J=2.4 Hz, 1H):

Workup

  1. customThe solvent was removed
  2. customto yield the crude, which
  3. customwas purified by recrystallization from THF-ether

Sources & evidence

ORD record
ord-5281de2aeddf43cd895faca3b98e4b91
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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