Tetrahydrofuran → HCID 54384606, compound

HRID 1003826Notes

Reaction equation

HRID 1003826 reaction equation
[OH:1][C@@:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([OH:6])=O.[C:21]([C:28]1NC=CN=1)(C1NC=CN=1)=[O:22].C1C[O:36][CH2:35]C1>>[CH3:35][O:36][C:21](=[O:22])[CH2:28][C:4](=[O:6])[CH2:3][C@:2]([OH:1])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 54497496HCID 54497496, compound

Product 1

HCID 54384606HCID 54384606, compound

Procedure

The title compound was prepared using (S)-3-hydroxy-3,5-diphenyl-pentanoic acid from Example AA (0.7 g, 2.59 mmol), THF (30 mL), and carbonyl diimidazole (0.5 g, 3.08 mmol). The reaction was stirred for 6 hours at room temperature; bis [3-methoxy-3-oxopropanoato (1-)-O,O'] magnesate from Example BB (0.8 g, 3.10 mmol) was added, and the reaction was stirred for 3 days at room temperature. The reaction was concentrated and the residue partitioned between EtOAc and 1N HCl. The organic layer was washed with aqueous NaHCO3 and brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography, eluting with EtOAc:hexane (20:80) gave the title compound. 1H NMR (CDCl3) δ 2.01 (m, 1 H), 2.11 (m, 1 H), 2.24 (m, 1 H), 2.64 (m, 1 H), 2.97 (d, 1 H), 3.28 (s, 2 H), 3.30 (d, 1 H), 3.64 (s, 3 H), 4.15 (s, 1 H), 7.03-7.42 (m, 10 H).

Workup

  1. customThe title compound was prepared
  2. stirringthe reaction was stirred for 3 days at room temperature
  3. concentrationThe reaction was concentrated
  4. customthe residue partitioned between EtOAc and 1N HCl
  5. washThe organic layer was washed with aqueous NaHCO3 and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography
  9. washeluting with EtOAc:hexane (20:80)

Sources & evidence

ORD record
ord-982d955eabe24be9a07bc3c1862b2b32
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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