Diethyl Ether → HCID 10781662, compound

HRID 480673Notes

Reaction equation

HRID 480673 reaction equation
C[O:2][C:3](/[CH:5]=[CH:6]/[C:7]1[C:8](=[O:23])[NH:9][C:10](=[O:22])[N:11]([C@H:13]2[O:18][C@@H:17]([CH2:19][OH:20])[C@H:15]([OH:16])[C@@H:14]2[F:21])[CH:12]=1)=[O:4].[OH-].[Na+].CCOCC>O>[C:3](/[CH:5]=[CH:6]/[C:7]1[C:8](=[O:23])[NH:9][C:10](=[O:22])[N:11]([C@H:13]2[O:18][C@@H:17]([CH2:19][OH:20])[C@H:15]([OH:16])[C@@H:14]2[F:21])[CH:12]=1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 10830253HCID 10830253, compound

Product 1

HCID 10781662HCID 10781662, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 15 (560 mg, 1.70 mmol) was stirred in a NaOH solution (2 N, 5 mL) at rt for 1.5 h, then diluted with water (20 mL) and neutralized with Dowex 50 w×8 (H+) resin. The mixture was filtered and washed with water and acetone. The combined filtrate was evaporated to dryness to give a pale-white solid, which was trituated with Et2O to give 16 as an off-white solid (450 mg, 84%): UV (MeOH) λmax 298.0,0 267.0 mn (sh); 1H NMR (CDCl3) δ 11.70 (s, 1H, NH, D2O exchangeable), 8.49 (s, 1H, H-6, j=8.1 Hz 7.22 (d, 1H, Ha, J=15.9 Hz), 6.73 (d, 1H, Hb, J=15.9 Hz), 5.89 (d, 1H, H-1′, J1′,F=16.8 Hz), 5.86 (d, 1H, 3′-OH, D2O exchangeable), 5.62 (bs, 1H, 5′-OH, D2O exchangeable), 5.05 (dd, 1H, H-2′, J2′,F=52.9 Hz), 4.18 (dm, 1H, H-3′, J3′,F=24.1 Hz), 3.89 (m, 3H, H-4′), 3.74 (m, 2H, H-5′).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with water and acetone
  3. customThe combined filtrate was evaporated to dryness
  4. customto give a pale-white solid, which

Sources & evidence

ORD record
ord-ab6e39ca66f048599f52c28ad123b799
Source dataset
uspto-grants-2003_11
Patent number
US06653318B1

Reaction notes

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