Water → HCID 67906924, compound

HRID 982478Notes

Reaction equation

HRID 982478 reaction equation
[OH:1][CH:2]([CH3:38])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:21]2[CH2:25][CH2:24][C@H:23]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[O:22]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19]Br)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5].[SH:39][C:40]1[NH:41][CH:42]=[CH:43][N:44]=1.[H-].[Na+].O>CN(C=O)C.C(OCC)C>[OH:1][CH:2]([CH3:38])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:21]2[CH2:25][CH2:24][C@H:23]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[O:22]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][S:39][C:40]2[NH:41][CH:42]=[CH:43][N:44]=2)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15078312HCID 15078312, compoundHCID 178527877HCID 178527877, compound

Product 1

HCID 67906924HCID 67906924, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of trans-2-[3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-(2-bromoethoxy)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (47 mg, 0.07 mmol)(Example 19A) in DMF (250 mL) was added to a mixture of 2-mercaptoimidazole (25 mg, 0.25 mmol) and NaH (56%; 10 mg, 0.25 mmol) in DMF (0.5 mL) under nitrogen, and the mixture was stirred at room temperature for 30 min. Water (5 mL) and ethyl ether (5 mL) were added, and the mixture was stirred for another 5 min. The ethereal layer was separated, dried over MgSO4, and filtered. The filtrate was evaporated to a residue, which was purified by preparative TLC (EtOAc) to give the title compound: Rf 0.5; MS, m/z 636 M+. ; NMR (CDCl3) δ 1.02 (t, CH2CH2CH3), 1.24 (d, CH2CHOHCH3), 1.85 (m, CH2CH2CH3), 2.0 and 2.49 (2 m, H-3 and H-4), 3.42 (m, CH2S), 3.54 (m, CH2CHOH) 3.84 and 3.88 (2 s, 3 OCH3), 4.18 (m, CH2CH2S), 4.3 (m, CH2CHOH), 4.38 (t, CH2CH2CH3), 5.22 (m, H-2 and H-5), 6.62 (s, C5ArH), 6.96 (s, NH), 7.1 (s, imidazole), 7.32 and 7.50 (2 d, J=1.5 Hz, C2ArH).

Workup

  1. stirringthe mixture was stirred for another 5 min
  2. customThe ethereal layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to a residue, which
  6. customwas purified by preparative TLC (EtOAc)

Sources & evidence

ORD record
ord-74116133555d4085aa6890147403efe5
Source dataset
uspto-grants-1991_02
Patent number
US04996203

Reaction notes

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