Phthalimide → HCID 12803194, compound

HRID 980289Notes

Reaction equation

HRID 980289 reaction equation
[N:1](C(OCC)=O)=NC(OCC)=O.[C:13]1([CH2:19][O:20][C:21](=[O:36])[NH:22][CH2:23][CH2:24][C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([CH2:34]O)[CH:32]=3)[NH:27][CH:26]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(=O)NC(=O)C2=CC=CC=C12>O1CCCC1>[C:13]1([CH2:19][O:20][C:21](=[O:36])[NH:22][CH2:23][CH2:24][C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([CH2:34][NH2:1])[CH:32]=3)[NH:27][CH:26]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20197302HCID 20197302, compound

Product 1

HCID 12803194HCID 12803194, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (1.48 g) in dry tetrahydrofuran (THF) (8 ml) was added over 2 min., keeping the temperature at 25°, to a stirred solution of phenylmethyl[2-[5-(hydroxymethyl)-1H-indol-3-yl]ethyl]carbamate (2.6 g), triphenylphosphine (2.35 g) and phthalimide (1.75 g) in THF (20 ml). After 4 h, the solvent was evaporated in vacuo and the residue was dissolved in a solution of hydrazine hydrate (15 ml) in ethanol (100 ml).

Workup

  1. customat 25°
  2. customthe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in a solution of hydrazine hydrate (15 ml) in ethanol (100 ml)

Sources & evidence

ORD record
ord-a978ec6ad51f486190c241e071ae036b
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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