Sodium methanolate methanol → HCID 69963309, compound

HRID 1745926Notes

Reaction equation

HRID 1745926 reaction equation
C([O:4][C@H:5]1[C@H:20]([O:21]C(=O)C)[C@@H:19]([CH2:25][O:26]C(=O)C)[O:18][C@@H:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C@@H:6]1[N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])(=O)C.C[O-].[Na+].CO>CO>[C:31]1(=[O:40])[N:30]([C@@H:6]2[C@@H:5]([OH:4])[C@H:20]([OH:21])[C@@H:19]([CH2:25][OH:26])[O:18][C@H:7]2[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]12

Participants

4

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 69963742HCID 69963742, compound

Product 1

HCID 69963309HCID 69963309, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 61a (26.0 g, 46.18 mmol) was treated with NaOMe/MeOH (25 wt. %, 2.7 mL) in MeOH (200 mL) at room temperature. After 6 h, the mixture was neutralized (IRC-50 resin, weak acid) and concentrated to give product 61b (20.0 g, 99%) as semisolids: 1H-NMR (500 MHz, CDCl3), δ 7.78–7.82 (m, 2H), 7.68–7.72 (m, 2H), 5.16 (d, J=8.5 Hz, 1H), 4.63 (d, J=4.5 Hz, 1H), 4.25–4.31 (m, 2H), 4.06 (dt, J=2.0, 8.5 Hz, 1H), 3.88–3.89 (m, 2H), 3.76 (dt, J=10.0, 6.5 Hz, 1H), 3.65–3.71 (m, 1H), 3.59 (s, 3H), 3.48 (t, J=6.5 Hz, 1H), 3.43 (dt, J=9.5, 3.5 Hz, 1H), 3.38 (dt, J=10.0, 6.5 Hz, 1H), 1.90–2.02 (m, 2H), 1.31–1.43 (m, 4H), 1.00–1.09 (m, 2H); 13CNMR (125 MHz, CDCl3), δ 174.0, 168.4, 134.0, 131.6, 123.4, 98.31, 75.53, 71.53, 71.20, 69.43, 61.63, 56.66, 51.38, 33.65, 28.84, 25.18, 24.34; HRMS (M+Na) calcd for C21H27O9NNa 460.1584. found 460.1598.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-bbcd9e5cecc34ebd8358e0bec92fe5c5
Source dataset
uspto-grants-2006_03
Patent number
US07019131B2

Reaction notes

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