Diethyl azodicarboxylate → HCID 53886350, compound

HRID 2290673Notes

Reaction equation

HRID 2290673 reaction equation
O[CH2:2][CH:3]1[O:7][C:6]2[CH:8]=[CH:9][C:10]([C:13](=[O:15])[CH3:14])=[C:11]([OH:12])[C:5]=2[CH:4]1[CH2:16][CH2:17][CH3:18].[SH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:33])[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:22][CH:21]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:33]=[C:26]([C:23]1[CH:22]=[CH:21][C:20]([S:19][CH2:2][CH:3]2[O:7][C:6]3[CH:8]=[CH:9][C:10]([C:13](=[O:15])[CH3:14])=[C:11]([OH:12])[C:5]=3[CH:4]2[CH2:16][CH2:17][CH3:18])=[CH:25][CH:24]=1)[CH2:27][CH2:28][C:29](=[O:30])[O:31][CH3:32]

Participants

5

Reactant 3

HCID 5462977Diethyl azodicarboxylateHCID 13745937HCID 13745937, compoundHCID 13922800HCID 13922800, compound

Product 1

HCID 53886350HCID 53886350, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound of Example 15 (1.4 g, 5.59 mmoles, 1 equivalent) and methyl 4-mercapto-γ-oxobenzenebutanoate (1.4 g) was taken up in 30 ml THF. This mixture was added dropwise to a 0° solution of 1.2 equivalent DEAD, (1.1 ml) and 1.2 equivalent (1.76 g) in 40 ml THF. The reaction mixture was stirred cold 30 minutes, then warmed to room temperature. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated, purified on a column of silica gel using 10/1 toluene/ethyl acetate to afford the title compound.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompurified on a column of silica gel using 10/1 toluene/ethyl acetate

Sources & evidence

ORD record
ord-5727e309ca114280a40fedbba469be8e
Source dataset
uspto-grants-1986_10
Patent number
US04617407

Reaction notes

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