Phthalimide → HCID 70087445, compound

HRID 429662Notes

Reaction equation

HRID 429662 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[C:11]=2[CH:10]=[C:9]1[CH2:27]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[C:11]=2[CH:10]=[C:9]1[CH2:27][N:33]1[C:29](=[O:39])[C:30]2=[CH:38][CH:37]=[CH:36][CH:35]=[C:31]2[C:32]1=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70089490HCID 70089490, compound

Product 1

HCID 70087445HCID 70087445, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 1-tert-butoxycarbonyl-2-hydroxymethylindole-4-carboxylate (465 mg), phthalimide (179 mg) and triphenylphosphine (640 mg) in tetrahydrofuran (15.0 ml) was added diethyl azodicarboxylate (425 mg) and the mixture was stirred at ambient temperature for 1 hour. The resulting mixture was concentrated in vacuo and the residue was chromatographed on silica gel with n-hexane:ethyl acetate (6:1). The solid was triturated with methanol to give benzyl 1-tert-butoxycarbonyl-2-phthalimidomethylindole-4-carboxylate (440 mg).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica gel with n-hexane:ethyl acetate (6:1)
  3. customThe solid was triturated with methanol

Sources & evidence

ORD record
ord-7abeee054d8a403b8e0d83c1a5fc7c73
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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