Hydrochloric Acid → HCID 89651135, compound

HRID 2174226Notes

Reaction equation

HRID 2174226 reaction equation
[CH2:1]([NH:3][C:4](=[O:25])[NH:5][C:6]1[CH:16]=[C:15]([NH:17][C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)[C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][N:7]=1)[CH3:2].Cl>[OH-].[Na+]>[CH2:1]([NH:3][C:4](=[O:25])[NH:5][C:6]1[CH:16]=[C:15]([NH:17][C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)[C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89650477HCID 89650477, compound

Product 1

HCID 89651135HCID 89651135, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of compound vii (0.140 g, 0.410 mmol) in aqueous sodium hydroxide solution (2M, 3 mL) was heated to 75° C. for 48 h, cooled to 0° C. and acidified to pH ˜2 using concentrated hydrochloric acid (35%). The resulting colourless precipitate was filtered, washed with water (3 mL) and air dried to give the desired compound viii. (0.116 g, 0.369 mmol, 90%) as a colourless powder, 1H NMR (300 MHz, DMSO-d6): δ 9.98 (1H, br s), 9.17 (1H, br s), 8.58 (1H, s), 7.94 (1H, br t), 7.30 (1H, t, J 7.7), 7.20 (1H, s), 7.12-7.06 (2H, m), 7.01 (1H, d, J 7.7), 3.13 (2H, dq, J 6.7 and 7.7), 1.05 (3H, t, J 7.2); [M+H]+ m/z=315.1.

Workup

  1. temperaturecooled to 0° C.
  2. filtrationThe resulting colourless precipitate was filtered
  3. washwashed with water (3 mL) and air
  4. customdried

Sources & evidence

ORD record
ord-96e6beb1a50f470295bde920d19fd7e5
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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