Hydrochloric Acid → HCID 57835870, compound

HRID 731188Notes

Reaction equation

HRID 731188 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C@H:26]([C:32]#[C:33][CH3:34])[CH2:27][C:28]([O:30]C)=[O:29])=[CH:22][CH:21]=2)[CH2:14][CH2:13]3)[CH:7]=[CH:8][CH:9]=1)[CH3:2].[OH-].[Na+].Cl>C1COCC1.CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH:15]([O:19][C:20]2[CH:21]=[CH:22][C:23]([C@H:26]([C:32]#[C:33][CH3:34])[CH2:27][C:28]([OH:30])=[O:29])=[CH:24][CH:25]=2)[CH2:14][CH2:13]3)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57835769HCID 57835769, compound

Product 1

HCID 57835870HCID 57835870, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 59.3 in THF/MeOH (1:1, 2 mL), was treated with 2N NaOH aqueous solution (1 mL) and stirred for overnight at room temperature. The reaction mixture was acidified with aqueous 4N HCl and extracted with EtOAc to obtain 59, which was purified by preparative HPLC, eluting with 5˜95% ACN in water containing 0.1% TFA. MS ESI (neg.) m/e: 439.1 (M−H). 1HNMR (MeOD-d4) δ 7.65 (br, 1H), 7.48 (s, 1H), 7.38 (d, 1H, J=7.02 Hz), 7.32 (t, 1H, J=7.12 Hz), 7.18 (d, 1H, J=6.57 Hz), 7.14 (s, 1H), 7.06 (m, 2H), 6.99-6.86 (m, 2H), 6.78 (m, 1H), 4.79 (m, 1H), 4.12 (q, 2H, J=6.50 Hz), 3.86 (m, 1H), 3.15-3.01 (m, 2H), 2.54-2.42 (m, 2H), 2.03 (m, 1H), 1.74 (ss, 3H), 1.42 (t, 3H, J=6.74 Hz).

Workup

  1. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-105c444eb534496c8dd1a3a785eb69a8
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

Loading…