Sodium Hydroxide → HCID 59752996, compound

HRID 750027Notes

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]([C:27]3[O:31][CH:30]=[N:29][CH:28]=3)=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.[OH-].[Na+]>CO.O>[O:31]1[C:27]([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:28][N:29]=[CH:30]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the product (90 mg, 0.21 mmol) from step 2 in 4:1 mixture of MeOH/water (2 mL) was added 2M solution of NaOH (124 uL 0.25 mmol). Reaction mixture was heated at 50° C. for 16 h. Solvent was removed in vacuo, residue was dissolved in water and pH was adjusted to 4-5 with 1M HCl solution. Then product was extracted with EtOAc, washed with water, brine, dried over anhydrous MgSO4 and concentrated to give the title compound (9.5 mg, 11%): MS; m/z 423.8 (M+H); 1H NMR (400 MHz, DMSO-d6); δ 1.20-1.30 (m, 2H), 1.82-2.25 (m, 6H), 2.73 (t, 2H, J=7.2 Hz), 3.17 (br, 2H), 3.75 (br, 1H), 4.21-4.27 (m, 2H), 7.01 (dd, 2H, J1=6.8 Hz. J2=2.4 Hz), 7.07-7.08 (m, 4H), 7.59 (s, 1H), 7.71 (dd, 2H, J1=6.8 Hz, J2=2.4 Hz), 8.41 (s, 1H); HPLC (UV); 86%.

Workup

customReaction mixture
customSolvent was removed in vacuo, residue
dissolutionwas dissolved in water
extractionThen product was extracted with EtOAc
washwashed with water, brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-43878555112f4c5fadaf6f8af3890209
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402684B2

Reaction notes

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