Solketal → HCID 67175763, compound

HRID 1027491Notes

Reaction equation

HRID 1027491 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:42]=[CH:41][C:17]([CH2:18][C:19]2[N:20]=[C:21]([O:37][CH2:38][CH2:39][CH3:40])[C:22]3[N:27]=[C:26]([C:28]4[CH:33]=[C:32]([CH3:34])[C:31]([OH:35])=[C:30]([CH3:36])[CH:29]=4)[O:25][C:23]=3[N:24]=2)=[CH:16][CH:15]=1.[CH3:43][C:44]1([CH3:51])[O:48][CH:47]([CH2:49]O)[CH2:46][O:45]1.C(N(CC)CC)C>O1CCCC1>[Cl:13][C:14]1[CH:42]=[CH:41][C:17]([CH2:18][C:19]2[N:20]=[C:21]([O:37][CH2:38][CH2:39][CH3:40])[C:22]3[N:27]=[C:26]([C:28]4[CH:29]=[C:30]([CH3:36])[C:31]([O:35][CH2:49][CH:47]5[CH2:46][O:45][C:44]([CH3:51])([CH3:43])[O:48]5)=[C:32]([CH3:34])[CH:33]=4)[O:25][C:23]=3[N:24]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7528Solketal2×HCID 8471TriethylamineHCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 136175016HCID 136175016, compound

Product 1

HCID 67175763HCID 67175763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 0.736 mmol of polystyrene-bound triphenylphosphine (Argonaut) and 128 mg of diethyl azodicarboxylate in 10 ml of tetrahydrofuran was stirred for 15 min at 0° C. Then 260 mg of 4-[5-(4-chloro-benzyl)-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenol, 81 mg of (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol and 85 μl of triethylamine were added. The reaction mixture was stirred at room temperature for 3 h. Then another 81 mg of (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol, 0.736 mmol of polystyrene-bound triphenylphosphine and 128 mg of diethyl azodicarboxylate were added and the reaction mixture was stirred for 18 h. The polymer was filtered off and washed thoroughly with tetrahydrofuran. The solvent was removed in vacuo and the title compound isolated by silica gel chromatography (method SC1) and then by preparative HPLC (method HPLC2).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 h
  2. stirringthe reaction mixture was stirred for 18 h
  3. filtrationThe polymer was filtered off
  4. washwashed thoroughly with tetrahydrofuran
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-31290207bbfe49539d7fa450462982fc
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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