Phthalimide → HCID 19605122, compound

HRID 1603486Notes

Reaction equation

HRID 1603486 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:11][C:12]([CH2:15]O)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:11][C:12]([CH2:15][N:21]2[C:20](=[O:22])[C:19]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]3[C:17]2=[O:27])=[CH:13][N:14]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19605146HCID 19605146, compound

Product 1

HCID 19605122HCID 19605122, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 20 ml of a THF solution containing 1.06 g of 2-(N-t-butoxycarbonylamino)methyl-5-hydroxymethylthiazole, 959 mg of phthalimide, 1.7 g of triphenylphosphine and 1.03 ml of diethyl azodicarboxylate were added, and the mixture was then stirred at room temperature for 1 hour. Then, the solvent was evaporated under reduced pressure, and the resulting residue was purified by a silica gel column chromatograph and Cephadex LH-20 in succession to obtain 1.02 g of 2-(N-t-butoxycarbonylamino)methyl-5-phthalimidomethylthiazole.

Workup

  1. additionwere added
  2. customThen, the solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by a silica gel column chromatograph and Cephadex LH-20 in succession

Sources & evidence

ORD record
ord-57ecde7ad31f4d16b98d4eb51e1ccb60
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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